May 11, 2026

What a Builder Insider Knows About Tampa Real Estate That Most Agents Don't | Craig Kincheloe

**EPISODE 322 — CRAIG KINCHELOE | THE KINCHELOE GROUP**
*Tampa Bay Real Estate | New Construction | Luxury | Investment*

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Craig Kincheloe didn't start in real estate — he started inside it. At 22 he joined KB Home, ranked top 3% nationally, and helped build entire Tampa Bay communities including Southfork, Southbay Lakes, and Churchill Bend. Before 30 he had been part of over 1,000 transactions. Today he leads the Kincheloe Group at REAL Broker specializing in luxury, new construction, and high-rise condos across Tampa Bay.

**What you'll learn:**

**New Construction Secrets** — Craig spent five years on the builder side. He breaks down how builders structure incentives, why they'll never cut price before offering upgrades and rate buydowns first, and how to negotiate deals most buyers don't know exist.

**Florida Condo Landmines** — Craig calls high-rise condo purchases "the most complex residential transaction in Florida right now." Post-Surfside legislation, reserve requirements, and HOA financial health have created a minefield most agents can't navigate.

**Tampa's Development Boom** — Gas Worx, West Riverwalk, and billions in new downtown investment are reshaping Tampa. Craig shares where he's personally investing and how to get ahead of appreciation before the window closes.

**Relocating to Tampa?** — Craig has lived in over a dozen Tampa neighborhoods. He tells out-of-state buyers from New York, Chicago, and D.C. exactly what they get wrong before they make a costly mistake.

**The Advisor Difference** — Proof over promise. Craig's consultation approach, fiduciary philosophy, and data-driven strategy are why he keeps breaking records in a corrective market.

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📲 kincheloegroup.com | @craigkincheloe

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Is Florida real estate really a buyer’s market or does the answer depend entirely on the property type location and strategy?

In this episode of the Real Estate Excellence Podcast, Tracy Hayes sits down with Craig Kincheloe. Craig Kincheloe is a Tampa native luxury real estate specialist licensed lender and former new construction sales expert with more than 23 years of experience in Florida real estate. In this episode Craig shares how he evolved through every major market shift from the 2008 housing crash to short sales investing luxury real estate and navigating today’s changing condo and insurance landscape.

Craig explains why market conditions vary dramatically depending on property type neighborhood and price point. He shares insider builder negotiation strategies luxury listing marketing techniques the growing role of AI in real estate and why understanding data and buyer psychology creates better outcomes for clients. The conversation also dives into condo assessments Florida insurance challenges and the hidden opportunities available in today’s market.

If you enjoyed this episode, be sure to subscribe share this episode with another real estate professional and leave a review for the Real Estate Excellence Podcast.

Highlights

00:00 - 05:18 Florida Market Trends and Buyer Conditions

  • Why every market depends on property type
  • The impact of inventory and location differences
  • How pricing changes by neighborhood and zip code
  • Why some homes sell immediately while others sit
  • Understanding today’s buyer versus seller market

05:18 - 13:42 Craig’s Real Estate Journey and Builder Expertise

  • Starting in real estate at 22 years old
  • Learning sales through new construction communities
  • Understanding how builders think and operate
  • Why builder negotiations are completely different
  • Hidden incentives buyers miss without representation

13:42 - 21:50 Surviving the Crash and Building Through Short Sales

  • Transitioning during the 2008 housing collapse
  • Helping investors buy builder inventory creatively
  • Launching a short sale negotiation company
  • Managing over 120 distressed listings at once
  • Why relationships mattered during difficult negotiations

21:50 - 34:12 Luxury Buyers Data and AI in Real Estate

  • Using market data to guide buyer decisions
  • How rare properties create urgency for buyers
  • Working with high-net-worth luxury clients
  • Using AI to strengthen negotiation strategies
  • Why local expertise still beats artificial intelligence

34:12 - 47:36 Breaking Records and Marketing Luxury Listings

  • Creating buyer avatars for luxury properties
  • Selling homes far above neighborhood comps
  • Why storytelling creates emotional connection
  • Fixing expired listings through better presentation
  • How staging lighting and positioning affect sales

47:36 - 01:00:00 Florida Insurance Condo Risks and Market Opportunities

  • Why insurance rates may finally be stabilizing
  • Preparing buyers for inspection and insurance issues
  • The complexity of Florida condo transactions
  • Reviewing condo financials and structural reports
  • Using AI tools to analyze condo health

Top of FormBottom of Form

Quotes:

“No deal is the same. No transaction’s the same.” – Craig Kincheloe

“We fall to the level of our systems and processes.” – Craig Kincheloe

“The best predictor of the future is the past.” – Craig Kincheloe

“Each showing is more valuable. You have to make the most of each showing as an agent.” – Craig Kincheloe

To contact Craig Kincheloe, learn more about his business, and make him a part of your network, make sure to follow his Website, Instagram, Facebook, and LinkedIn.

Connect with Craig Kincheloe!

Website: https://kincheloegroup.com/about

Instagram: https://www.instagram.com/craigkincheloe/

Facebook: https://www.facebook.com/CraigKincheloe

LinkedIn: https://www.linkedin.com/in/craigkincheloe/

Connect with me!
Website: toprealtorjacksonville.com

Website: toprealtorstaugustine.com

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Are you ready to take your real estate game to the next level? Look no further than Real Estate Excellence - the ultimate podcast for real estate professionals. From top agents and loan officers, to expert home inspectors and more, we bring you the best of the best in the industry. Tune in and gain valuable insights, tips, and tricks from industry leaders as they share their own trials and triumphs. Whether you're a seasoned pro or just starting out, a homebuyer or seller, or simply interested in the real estate industry, Real Estate Excellence has something for you. Join us and discover how to become a true expert in the field.

The content in these videos and posts are for informational and educational purposes only. The information contained in the posted content represents the views and opinions of the original creators and does not necessarily represent the views or opinions of Townebank Mortgage NMLS: #512138.

REE #322 Transcript

[00:00:00] Craig Kincheloe: No deal is the same. No transaction is the same. You're constantly finding yourself in new experiences, and you're constantly learning something new every day, every transaction. I do my best to debrief after the transaction and say, “All right, what went well? What could we have improved upon?” Then I look at my systems and processes because everybody on my team knows I say it over and over again: we fall to the level of our systems and processes.

[00:01:00] Tracy Hayes: Hey, welcome back to the Real Estate Excellence Podcast. My guest today started in real estate at the age of 22, and before he turned 30, he had been part of over a thousand transactions. He didn't just sell Tampa Bay, he helped build it, literally branding and selling entire communities that are now on the map.

[00:01:20] Tracy Hayes: Today, he's a Tampa native, licensed lender, luxury specialist, and one of the most well-rounded real estate minds in the state of Florida. From new construction to luxury condos to relocation, this conversation covers it all. Let's welcome Craig Kincheloe to the show.

[00:01:38] Craig Kincheloe: Thanks for having me on, Tracy. Looking forward to our conversation.

[00:01:40] Tracy Hayes: Yeah, definitely. I think there's a lot in there because everything you've experienced is a hot topic right now in Florida. I'm over here in Jacksonville, you're over there in Tampa, and I think they're under similar demand, especially with a lot of new construction going on. I'm sure you have some insights on that.

One of the questions we’re going to talk about today is whether it’s a buyer’s market. That’s a trending question right now. Is it a buyer’s market? Well, it depends on the price point right now. Would you agree?

[00:02:15] Craig Kincheloe: Yes. Even more than that, the way I like to describe it is that it depends on the property type first. Are we talking about a single-family home, or are we talking about a condo, townhome, villa, or whatever the property type may be? That’s where I start.

Then it comes down to price range, as you mentioned, and then location. Location could mean a neighborhood, a zip code, or even streets within geographic boundaries. It’s all over the place, so you can’t answer that question accurately in today’s market without defining it more specifically.

When somebody tries to answer that question straight up, it tells me they lack knowledge and experience.

[00:02:52] Tracy Hayes: Yeah. We’re definitely seeing that the right houses — basically what you’re describing — the right house on the right street, in the right zip code, whether it’s a townhouse or single-family home, if it’s priced right and has the right location, it could go the first weekend, while others are sitting for 30, 45, even 60 days.

[00:03:13] Craig Kincheloe: Yeah, it’s wild. I could look at properties within a one- to two-mile radius of each other — so you’d think they’re in pretty similar locations, right?

[00:03:21] Tracy Hayes: Yeah.

[00:03:21] Craig Kincheloe: I could look at one area and say, “All right, there are 15 properties for sale in this neighborhood or building, and over the last six months only one sold.” Then within a mile away, I could say, “There are four for sale, but over the last six months there have been 24 sales.”

Not to get too technical, but in the real estate industry we use something called “months supply of inventory.” Basically, all that means is if no new homes were listed for sale, based on the current monthly sales rate, it would take a certain number of months to sell all the homes currently on the market.

In that first example, there’s about a seven-and-a-half-year supply of inventory, which is actually worse than the Great Recession we experienced in 2008, 2009, and 2010. Then in the other situation, it was more like a one-and-a-half-month supply of inventory.

That’s mind-blowing when you think about the numbers and how they can exist in similar locations. So you really have to look at that carefully.

[00:04:25] Tracy Hayes: Yeah, so there’s definitely not a straight answer to that question. I totally agree, and we’re experiencing the same thing over here. I imagine other parts of Florida are as well.

People are looking for very specific things, and if a property fits what they want — the right schools, the right location, whatever it may be — it’s gone.

Let’s go back a little bit and talk about how you got into real estate. You started in new construction, which I think is a home run for a young person wanting to get into real estate, especially someone who maybe hasn’t even bought their first home yet and doesn’t know much about the business.

Did new construction really help you get off the ground and give you a solid foundation to launch your career?

[00:05:06] Craig Kincheloe: Yeah, absolutely. I got licensed when I was in college. I was a junior during the summer when I got my license. Shortly after that, I actually dropped out of college.

I got my mortgage license and did that for about a year and a half while I was getting into the new construction industry. It was a tough job to land as a young 22-year-old when the market was booming back in 2003 and 2004, but I finally got the opportunity.

It taught me a lot because I was selling so many homes in such a short period of time. I sold in nine communities, and we were developing so much. Then I became a manager for another homebuilder where we were building around 700 to 800 homes just in that division.

It gave me a tremendous amount of experience very quickly. It taught me how builders think, how they run their businesses, and all of those things now help my clients because builders operate very differently than a typical seller.

[00:06:01] Tracy Hayes: For someone thinking about getting into the business, I think the podcast speaks both to people who are brand new and those who’ve been in the business for a while but maybe haven’t gotten the “at-bats” you got early in your career.

You obviously took advantage of those opportunities, and it’s made a huge difference. You’ve now been in the business for about 23 years, right?

[00:06:26] Craig Kincheloe: Yeah, 23 years.

[00:06:29] Tracy Hayes: Having that confidence early on — because, like you said, you were in the model homes and people were coming to you — is very different from where you are today, where you spend most of your time marketing and working with clients.

Back then, the builder handled the marketing, the subdivision was already there, and you were just practicing every day with new customers coming in. You were practicing your presentation, your handshake, and everything else. How much did that help build your confidence as a young person in such a demanding industry?

[00:06:58] Craig Kincheloe: That’s a great question. They’re very different skill sets in a lot of ways.

When I had a real estate team and was hiring agents, I hired some people from new construction sales, and many of them struggled because it really is a different skill set.

As you mentioned, when you’re working for a homebuilder, the sales process is very different. You have a captive audience because the builder spends the marketing dollars to get people to come to you. They typically walk through your model home, and then you have a product or products you need to sell them.

Versus general real estate, where you have to proactively go out and find clients yourself. Usually, you’re responsible for your own marketing, lead generation, and whatever strategies you use to attract clients.

[00:07:41] Tracy Hayes: Mm-hmm.

[00:07:41] Craig Kincheloe: A lot of salespeople from the new home industry don’t like that side of the business. They’re not comfortable with it. So they struggle, and many times they go back into the new home industry. Those are very different things.

The thing I liked about the new home industry is that it helped me understand the product at a high level.

[00:08:00] Craig Kincheloe: Right. I needed to understand the quality of the build, the finishes, and all the things that go into it. Most real estate agents, if they don’t have that background, don’t have the knowledge or skill set that I gained from the homebuilding industry, and I’m very grateful for that.

[00:08:15] Tracy Hayes: Have you seen — because I think you spent about five years or so in new construction?

[00:08:19] Craig Kincheloe: Yeah, right around there, about five years.

[00:08:19] Tracy Hayes: The incentives builders are giving today — I mean, during that time period, if I remember correctly from your LinkedIn, you were in new construction up until about 2007.

[00:08:33] Craig Kincheloe: Yeah, the end of 2007.

[00:08:35] Tracy Hayes: So you started to see the market fall off around that time. But the incentives builders are offering today — have you ever seen anything like it? The amount of money they’re giving to attract buyers, and not only buyers but also agents to bring in business right now?

[00:09:00] Craig Kincheloe: Yeah, it’s incredible. I got a little bit of that at the tail end of my career in the new homebuilding industry because the market started to shift. I was in Sarasota at the time, and that market shifted sooner than a lot of other Florida markets.

We were doing 3-2-1 buy-downs, selling the payment back then, emotional staging, and a lot of creative things. We were offering real estate agent bonus commissions and things like that. So I got to understand how to navigate a challenging market while still being able to sell and move homes.

In fact, we had 120 finished inventory homes, and management wanted us to sell them within six months. We sold them in about 90 days by selling the payment — making the monthly payment affordable for people.

That’s what builders are doing today, and most of the best opportunities right now are on the new construction side.

Most people don’t realize this — and I don’t want to get too technical — but builders have an unfair advantage compared to a normal seller because they can pre-buy mortgage money to get interest rates down.

If you’re buying a resale home, you can ask the seller to contribute toward closing costs and use that money to buy down the interest rate, but there are limitations depending on the loan program. Usually it’s around 3% to 6%, depending on your down payment. So there’s a finite amount of money available to reduce the rate.

But builders go to lenders in advance and say, “I’m going to buy $5 million or $10 million worth of mortgage money,” usually for an entire neighborhood or division. They can apply that off the closing statement, so you can still get your 3% to 6% seller concession, while also getting rates down to 3.9% or 4.25% on a 30-year fixed mortgage.

Builders are simply able to outmaneuver a typical seller. So if you’re a buyer, you want to take advantage of that because you can get a great payment right now.

[00:11:01] Tracy Hayes: Tell us — and sell yourself a little bit here — because I think this is important. As you and I know, there are still people who literally just walk into a model home and work directly with the site agent.

You’ve been a site agent, and now you’re a successful team leader and agent yourself. Why is it important, especially with all these incentives available, for buyers to connect with someone like you to guide them through the process?

[00:11:28] Craig Kincheloe: As I mentioned before, negotiating with a builder is very different from negotiating with a normal seller.

I have insider knowledge about how builders operate. Most large builders are publicly traded companies, so they have shareholders, forecasting numbers, fiscal-year deadlines, and quarterly goals.

If you understand that — along with where they are in their numbers and the right questions to ask their salespeople — you can negotiate incredible deals, especially in today’s market.

Another thing is understanding that builders would rather give free upgrades, special financing, or closing cost incentives than reduce the actual price. If they reduce the price, that reduction gets recorded in public records through the property appraiser, and it affects future comparable sales.

So you have to understand those dynamics and know how to negotiate properly.

You can get really strong deals right now if you understand builder margins and realize that some builders will sell homes at a loss near the end of their fiscal year if they can close and deliver the home. They do not want finished inventory carrying over into the next fiscal year.

At that point, if they don’t already have a higher offer, they’re often going to seriously consider whatever reasonable offer you make.

[00:12:56] Tracy Hayes: Right, right. It sounds like a car dealership.

[00:12:59] Craig Kincheloe: Yeah.

[00:13:00] Tracy Hayes: They work the same way. They’ve got to get those end-of-the-month units out. In this case, people don’t realize that once you have a completed home with a certificate of occupancy and it becomes January 1st in Florida, you’re now paying the higher taxes on it.

[00:13:19] Craig Kincheloe: Absolutely. One of my friends is a top sales rep for a large homebuilder, and he told me they look at finished inventory like perishable food sitting on a shelf. The longer it sits there, the less it’s worth, and eventually they’ll have to keep discounting it.

So they want to get finished inventory off their books quickly, separate from their quarterly and yearly forecasting numbers.

[00:13:50] Tracy Hayes: There’s no doubt, for anyone listening right now, that you need to get connected with someone like Craig. He obviously knows the Tampa area, he’s been on both sides of the business, and he’s been doing this for decades.

To sit down and have a buyer consultation with someone like you — and understand which neighborhoods are ideal or hot right now — is huge. Because you’ve been in the business long enough, you also have connections, like your friend working for one of the builders.

You know where the soft spots are and where buyers can get the best financial deal on the right home.

[00:14:28] Craig Kincheloe: Absolutely. Relationships are key because builders don’t put all their inventory online.

Even when you walk into the model home, they often won’t show you all their inventory because they want to create a sense of scarcity.

Understanding that and knowing how to navigate it is important.

I’ve had buyers go look at homes without me, and maybe they negotiate a little bit on their own. Then they call me afterward, and I’m able to negotiate a significantly better discount simply because I understand how to speak the builders’ language.

Most sales reps, if you have good relationships with them, want to sell a home. So they’ll often give you insights if you know the right questions to ask.

[00:15:14] Tracy Hayes: Yeah, like I said, not every builder is the same either. Knowing where their soft spots are — whether it’s appliances, fixtures, upgrades, or whatever incentives they can offer — that’s the knowledge and value you bring to the table.

Do not go into new home construction without representation.

All right, 2007 happens. Obviously, we know the market is starting to go sour, but you decide to move out of new construction and into what I call “retail real estate.” What was happening in your life at that point, and what made you want to make that change?

[00:15:50] Craig Kincheloe: My original plan when I got my license was to become a new home salesperson, work my way up to vice president of sales, then division president, and eventually break out on my own to become a homebuilder and developer. That was the path.

Then, obviously, 2007 happened.

They created a role for me called Portfolio Manager, which allowed me to manage all the inventory homes across different neighborhoods within that division. I really loved the role and enjoyed it.

But once we sold through all the inventory homes, they drastically reduced production. We went from around 250 employees down to about 50 employees.

For someone in their early twenties, it was eye-opening to see so many good people — people who had been with the company for over 20 years — get laid off despite being excellent at their jobs.

Once we sold the remaining inventory, they wanted to place me back into a neighborhood sales role, but they were only releasing maybe a couple of new home starts per month. So no matter how hard I worked—

[00:17:00] Tracy Hayes: Yeah.

[00:17:03] Craig Kincheloe: I could only sell maybe one or two homes a month at most, especially since I had a sales partner. My income would have dropped to maybe one-third — or more realistically one-quarter — of what I had been making.

So I decided I either needed to power through knowing my income would significantly decrease, or look for other opportunities.

I used my knowledge of builders and went out on my own. I found investors who wanted to buy builder inventory, and we created a very creative structure that worked for the builders because it didn’t slash publicly recorded prices, which protected values for existing homeowners.

At the same time, it worked for the investors because they were still able to buy at favorable pricing through the structure we created.

I ended up selling a lot of real estate over about a year doing that.

[00:18:00] Tracy Hayes: So you kept afloat while a lot of others were dropping out of the business during that 2007, 2008, 2009 time period.

[00:18:09] Craig Kincheloe: Exactly. One thing you’ll see throughout my career is constant evolution with the market.

You have to evolve if you want to survive in real estate because the market conditions, economy, and opportunities are always changing.

[00:18:27] Tracy Hayes: Yeah.

[00:18:27] Craig Kincheloe: After that, I evolved again and started a short sale company with business partners who were in the lending industry.

We created a company called Short Sales for Agents, and we negotiated short sales on behalf of agents throughout Florida.

Then I transitioned into personally listing short sales. At one point, I had over 120 short sale listings across eight or nine counties in Florida.

My career has been very evolutionary.

Eventually, that transitioned into selling distressed properties to investors. Then I started thinking, “Why am I making all these investors money? I should be buying some of these properties myself.”

So I got into investing, flipping properties, and holding rentals during that period.

Then, eventually, the short sale wave came to an end — like many things in real estate do — so I evolved again into what I’m doing now: traditional retail real estate.

[00:19:30] Tracy Hayes: One of the things you mentioned was having over 120 short sales going at the same time.

My wife and I bought a foreclosure at the end of 2008. I remember specifically because I was working at Quicken Loans at the time. Around Halloween of 2008, a 30-year fixed rate was around 6.25%. By the time we made our offer — the day before Thanksgiving — rates had dropped to around 5.375%, and I remember saying, “Oh my God, I’ve got to lock this in.”

The rates obviously continued downward afterward.

Fortunately, the agent involved in our transaction had a direct connection to the person at the bank making the decisions. We got a response within a day or two, which I imagine was very rare back then.

What did you learn that helped move short sales along so they weren’t sitting for six to twelve months without answers from the banks?

[00:20:40] Craig Kincheloe: It starts with having a complete and organized short sale package. The number one reason short sales got delayed was incomplete documentation.

Second, it was understanding what the banks were looking for.

I knew what Fannie Mae and Freddie Mac would accept based on the BPO — Broker Price Opinion. They’d usually send out a real estate agent to evaluate the property rather than a full appraiser.

I would meet those agents at the property and influence the valuation by providing repair estimates and other supporting information to help position the file for approval.

Then there were the relationships.

I used software to identify people within the banks and lenders, and I also became a Certified Distressed Property Expert (CDPE). I coached with Alex Charfen and Katie Charfen, who founded that program.

At one point, I was handling a luxury short sale involving three mortgages totaling nearly $4 million, all with the same lender.

I was at a conference in Las Vegas, and a guy from that lender was speaking on stage. Afterward, I literally followed him toward the bathroom and told him about the short sale because the bank kept telling me the file was in “executive review” for weeks with no progress.

He looked at me and said, “Well, I am the executive review.”

And just like that, after being stuck for weeks, the file finally moved forward and got approved.

It involved a well-known celebrity, and we were able to complete the transaction discreetly without ever putting the property on the market, so it protected the client’s privacy. It was a win-win.

A lot of things in life — and in business — come down to relationships.

[00:22:47] Tracy Hayes: When you went to that conference, did you know he was actually the decision-maker, or did you just know he worked for the lender?

[00:22:57] Craig Kincheloe: I had no clue. I just knew he worked for the lender and seemed pretty high up. I was honestly dumbfounded when he said, “I am the executive review.”

At first, I wasn’t even sure if he was serious.

[00:23:10] Tracy Hayes: Right. “Can we go have lunch?”

[00:23:15] Craig Kincheloe: Exactly.

[00:23:17] Tracy Hayes: We started the show talking about whether it’s a buyer’s or seller’s market. We’re seeing across Florida that some properties are hotter than others.

When you’re working with buyers today, there are always some people who think they’re going to steal a property far below asking price. At the same time, there are sellers who insist on pricing too high, and then the property just sits on the market and eventually sells for less than it probably would have if priced correctly from the beginning.

How do you coach buyers through that process? Maybe think of a recent example where one neighborhood gave buyers leverage while another nearby neighborhood didn’t. How do you help buyers structure offers that actually have a chance of getting accepted?

[00:24:38] Craig Kincheloe: I’m a very data-centric agent. Most agents are not. Everything for me comes back to data and what I can show clients objectively.

One thing I do that most agents don’t is extensive research.

I had a luxury client recently who was considering canceling a contract because of inspection issues. The property was at the end of a cul-de-sac on the Intracoastal Waterway with about 400 feet of waterfront views. It was spectacular.

[00:25:12] Tracy Hayes: Mm-hmm.

[00:25:13] Craig Kincheloe: There are only so many streets that have what we call “fingers” — those cul-de-sacs with homes at the very end of them. So I did a search over the previous four or five years to see how many of those types of homes had sold.

I told him, “I understand there are inspection issues, and those are valid concerns. However, if you want to be at the end of a cul-de-sac with 400 feet of waterfront, and you want these specific features, then understand that over the last four years there has only been one other home like this that sold.”

I said, “Before you cancel, just make sure those things truly aren’t important to you.”

After he closed and moved in, he told me, “I was 100% going to cancel, but that information changed my perspective.” And now he’s very happy there.

The point is that, as agents, we have to establish context.

If a client is looking for a specific type of property, we need to determine whether it’s a dime-a-dozen property or something truly unique. If the deal falls apart, are there going to be three more like it coming on the market next month, or could it be years before another one appears?

First, I need to understand their criteria and what’s absolutely required in the property. Then I establish historical data to determine how rare that type of property really is.

A lot of agents will just say, “Well, there’s only one for sale right now.”

Okay, but that’s only right now.

I go back historically because the best predictor of the future is the past. Maybe there’s only one available today, but historically there are many more that tend to come on the market regularly.

That approach works really well with buyers because it removes my opinion from the equation and replaces it with data.

[00:27:09] Tracy Hayes: Yeah.

[00:27:09] Craig Kincheloe: Ultimately, one of the hardest things for agents working with buyers in this market is creating urgency. A lot of buyers lack urgency.

I’m not trying to create false urgency where it doesn’t exist, but there absolutely are situations where urgency is warranted, and it’s my job to guide them through that.

[00:27:32] Tracy Hayes: You make me think of the phrase, “One in the hand is worth two in the bush.”

That property was unique. They don’t come up often. You had it under contract, and if he walked away, the fear of loss becomes very real.

Your market is unique because Tampa Bay has so much waterfront property — Intracoastal, canals, bayfront, and so on. You’ve got a lot of exposure to luxury homes and high-rise condos at very high price points.

We only have a few of those in Jacksonville compared to Tampa and St. Pete.

What have you learned from working with luxury home buyers over the last 20-plus years that has made you an even better agent for average buyers purchasing homes in the $500,000 to $600,000 range?

Because I imagine working with multimillion-dollar buyers forces you to fine-tune your knowledge, preparation, and professionalism. Otherwise, they’ll simply find another agent.

[00:29:10] Craig Kincheloe: Absolutely. Expertise and saving clients time are critical, especially with luxury buyers.

You have to understand what they value and be able to deliver on it.

There are generally a couple different types of luxury clients.

One group is extremely busy with their businesses or careers. They want a professional they can trust to handle everything, and they’ll be very hands-off during the process.

For those clients, you have to deliver exceptional communication, set clear expectations, and go above and beyond by handling as much as possible for them — finding vendors, getting quotes, coordinating with builders, and generally making their lives easier.

Then there’s another group that wants to be heavily involved in the process. They want collaboration because that’s often how they became successful in the first place.

Those clients force you to really be on your game and highly knowledgeable because now, especially with AI, they’re using advanced tools themselves.

I recently sold a condo for a woman who was a business consultant, and the process was extremely collaborative. She used AI for many different things, including negotiation strategies.

She would bring me frameworks and ideas generated by AI, and we’d discuss them together. I’d tell her, “This part is spot-on, this part doesn’t work, and here’s why.”

So it became a collaborative process where we combined her AI-generated research with my real-world market experience.

[00:30:57] Tracy Hayes: Can you think of a specific example? I’m curious what exactly she asked AI to help with and how you refined it.

[00:31:10] Craig Kincheloe: Sure. This condo had an $86,000 assessment attached to it.

Three years ago, the condo probably would have sold close to $1 million, but in today’s market it was more of an $800,000 condo.

It’s important to understand that while older condos are declining more sharply in value, this particular condo was built in 2007, so it wasn’t even subject to the milestone inspection requirements because it wasn’t old enough.

However, the reserve study identified structural issues, and there was a $6.5 million project underway for repairs.

She used AI to help frame the assessment as a benefit to the buyer instead of just an objection. We collaborated on positioning the value and explaining the long-term benefits of the repairs and improvements.

AI actually produced some useful positioning ideas that we incorporated into our marketing and negotiation strategy.

She also used AI when considering price adjustments. We would evaluate different strategies together, and while some of the suggestions were useful, others needed refinement based on real-world market conditions.

[00:32:33] Tracy Hayes: The condo had an $86,000 assessment, so obviously you had to overcome that objection.

But what people also need to understand with condos is that when you’ve got multiple sales in the same complex, those become your strongest comparable sales.

The building itself matters far more than another building farther down the beach because every unit in that complex is carrying the same assessment.

[00:33:12] Craig Kincheloe: Exactly. And the challenge was that nothing in that building had moved in several months. Everything was just sitting on the market.

So the question became: how do we differentiate our listing?

Historically, maybe there were only one or two condos listed for sale in that building at a time, but now there were six or more.

That’s where I really excel — figuring out how to differentiate a property and position it differently from the competition.

[00:33:41] Craig Kincheloe: I’m really good at understanding differentiation and crafting a compelling story that resonates with prospective buyers and motivates them to act.

That’s where I excel.

She came up with some useful ideas through AI, but often AI simply gives me starting points or concepts, and then I fine-tune them.

[00:34:04] Tracy Hayes: Yeah, absolutely. I use AI all the time myself for the show and for creating different kinds of content.

The better information you feed into AI, the better output you get. It’s like nutrition — the better food you eat, the healthier you are. AI works the same way.

If you don’t provide complete context, it only works from limited information, and sometimes you don’t want it pulling unrelated information from elsewhere because that can become dangerous in a real estate situation.

[00:34:36] Craig Kincheloe: Exactly.

My team uses AI constantly for our digital magazine, blog content, and marketing. But honestly, it’s wrong a lot of the time.

You really need to know what you’re doing. It’s no different than handing someone a race car — if they don’t know how to drive, it becomes dangerous very quickly.

AI is the same way.

It’s a challenge for our industry because our clients are using it too. So part of our job now is explaining where the AI is wrong and why it’s wrong.

Ultimately, it just means we need to become better at our jobs.

When online search portals first appeared, agents no longer controlled access to inventory. Buyers could suddenly search for homes on their own, so we had to elevate our game and provide more expertise and value.

AI is simply the next evolution of that.

[00:35:33] Tracy Hayes: Absolutely.

All right, here’s one of those questions that makes you reflect a little bit:

Walk me through something that happened recently — a deal, a client situation, or a negotiation — that surprised you, challenged you, or really stuck with you. Basically, one of those stories you tell at cocktail parties.

[00:35:58] Craig Kincheloe: There are so many.

One thing that stands out is the fact that I’m still breaking records in this market.

Not every sale is a record sale, but many of them are all-time records.

One recent example was on the listing side.

The seller had purchased the property for around $1.5 million a couple years earlier and completed a very high-quality renovation. But there simply were no comparable sales in the neighborhood — or even surrounding neighborhoods — that supported where I believed the value should be.

It was a single-story ranch-style home, and there are very few ranch homes left in South Tampa because most of them are being torn down and replaced.

On top of that, many homes in the area had flooded recently, but this particular property had not flooded despite being in a neighborhood where around 80% of the homes had.

So I knew that was a major selling point.

We priced the property nearly 60% higher per square foot than the next highest comparable sale in the neighborhood.

One thing I do is create buyer avatars.

Basically, I determine who the most likely buyer is going to be — where they’re from, their age range, whether they have kids, whether they’re empty nesters, whether they have pets, how they’ll use the property, and so on.

I actually share these projections with my sellers before we list the property. I tell them, “Here’s who I think is going to buy your home. Let’s see if I’m right.”

In this case, I told the seller, “The buyer who pays this price probably won’t have young kids. They’ll likely be empty nesters.”

The seller had children, but I pointed to a large oak tree in the backyard and said, “The future buyer is going to want to remove that tree and install a pool. I’m going to get an arborist out here ahead of time so we know whether it can be removed and what it would cost.”

The seller said, “But they won’t even have kids.”

And I said, “No, but they’ll want their adult children and grandkids to come visit them. They’ll likely be moving here from the Northeast.”

Before we even officially listed the home, I held a broker open.

The eventual buyers had moved from Long Island about ten months earlier, were empty nesters with grown children, and wanted to install a pool exactly where I had predicted.

It played out almost identically to the avatar I created.

We sold the property for full price.

I also negotiated the removal of the appraisal contingency because I knew there was no way the property would appraise at contract value.

Sure enough, the appraisal came in $150,000 below the purchase price, but the deal still closed because we had structured it properly.

That’s why when people ask whether it’s a buyer’s market or seller’s market, the answer is always: it depends.

There are absolutely situations where it’s still a strong seller’s market, especially when a property has true differentiation and is marketed correctly.

Luxury buyers will absolutely pay a premium for something unique if they can’t easily replace it with another option down the street.

[00:39:08] Tracy Hayes: How did you come up with the avatar?

Because most people listening are probably wondering how you predicted all of that so accurately.

[00:39:27] Craig Kincheloe: AI had absolutely nothing to do with it.

This is where real local expertise outperforms AI every single time.

The answer is simple: working directly with buyers.

For a period of time, I focused heavily on listings and became disconnected from what buyers were actually saying and wanting.

When I shifted back into actively working with buyers again, I realized how much market intelligence I gained from hearing their thoughts, concerns, motivations, and desires firsthand.

That knowledge made me significantly better when representing sellers.

That’s where the avatar came from — years of showing similar properties, understanding where buyers are moving from, how they want to live, and how they envision using a property.

[00:40:21] Tracy Hayes: That’s an incredible story.

Honestly, I’d take that whole clip and use it on your website because it’s such a strong example of your expertise and ability to see what others miss.

A lot of agents would’ve looked at that property and immediately told the seller to lower the price because there were no comps to support it.

Instead, you understood the buyer psychology and knew those buyers existed — you just had to find them.

[00:40:55] Craig Kincheloe: Exactly.

In fact, a very successful top-producing agent who lives in the neighborhood attended the broker open before we listed the property.

He didn’t know our asking price yet.

I asked him, “What do you think this home is worth?”

He said maybe $1.15 million, maybe $1.2 million at best.

We ultimately sold it for roughly $300,000 more than that.

And this wasn’t a novice agent — this was a top 1% producer.

[00:41:30] Tracy Hayes: That really speaks to your expertise.

A lot of agents are good agents, but many simply go through the motions. You’re clearly sharpening your skills constantly, and that’s why you’re able to create these kinds of outcomes for higher-end clients.

Let’s shift gears a bit because one of the biggest challenges in Florida right now is insurance.

The average homeowners insurance premium in Florida is reportedly three to four times the national average, but there are signs things may be stabilizing. Citizens has reduced some rates, new carriers have entered the market, and litigation has dropped significantly.

At one point, Florida reportedly had more property insurance litigation than the other 49 states combined.

From where you sit in Tampa, are things genuinely stabilizing, or are buyers and sellers still getting blindsided by insurance costs?

[00:42:29] Craig Kincheloe: For the first time in a very long time, I’m actually having clients tell me their renewal premiums are decreasing instead of increasing.

That hasn’t happened in years.

A lot of these changes started back in 2019 when Governor DeSantis and lawmakers finally began making legislative reforms around property insurance.

I’ll say they were late to the game, but changes were eventually made in 2019, and additional reforms followed in 2021 and 2022.

We’re finally starting to see the effects now.

A major factor has been limiting litigation and preventing contractors from abusing assignment-of-benefits agreements. There were several reforms implemented that are now helping stabilize the market.

[00:43:10] Craig Kincheloe: Insurance premiums are going down. I’m also seeing condo master insurance policies for high-rise buildings starting to decrease as well, which is definitely a positive sign.

That said, I still deal with insurance challenges all the time, especially with older homes.

You run into four-point inspection issues constantly — roofs, electrical wiring, plumbing, HVAC systems, and all those kinds of things.

Being able to navigate those issues is critical, and that’s why buyers and sellers need knowledgeable agents. Otherwise, deals can hit a wall and fall apart simply because the agent doesn’t know how to work through the insurance challenges.

[00:43:55] Tracy Hayes: If you’re advising your team or other agents right now — and I’d assume this is a best practice — are you proactively evaluating insurance concerns before properties even go under contract?

Coming from the lending side, as soon as I receive a contract, I’m immediately ordering insurance quotes because underwriting is going to require them anyway.

When you’re going on listing appointments and you see an older home with an aging roof or old systems, are you already discussing those issues with insurance agents upfront to identify potential problems before they become negotiation issues later?

[00:44:48] Craig Kincheloe: Yeah, and I’ll go slightly off track here before circling back.

Obviously, the relationship between real estate agents and commissions has evolved a lot recently, so my focus now is adding as much value as possible from the very first interaction with a buyer.

A lot of my clients come from referrals or past relationships, which is different. But if I receive an online lead from Zillow or another source, and a buyer wants to see a property before we’ve even spoken, I now run a very detailed process immediately.

First, I review all disclosures attached in the MLS. I even use AI frameworks to analyze disclosures and identify potential concerns.

Then I pull permit history because insurance companies care tremendously about permits now.

For example, maybe the roof was replaced three years ago, but if no permit was pulled, many insurance carriers won’t insure the property.

So before we even see the property, I’m trying to determine the ages of the roof, HVAC, water heater, and all major systems.

Most people don’t pull permits for water heaters, but I still gather all of that information because I want to save buyers time.

If insurance issues are going to eliminate a property from consideration, I’d rather know that upfront instead of after everyone is emotionally invested.

I always tell clients: “If you’re surprised by something during the process, then I didn’t do my job.”

My goal is for clients to know every upcoming step and every potential issue before it happens.

Once we identify potential insurance concerns, we can decide strategically whether to address them during the initial offer or save them for negotiation during the inspection period.

If it’s a competitive multiple-offer situation, maybe we approach it differently. There’s strategy involved.

But one way or another, the insurance issues need to be addressed early.

And yes, I absolutely try to get insurance quotes early in the process as well.

Most of my clients aren’t stretching to their maximum loan-to-value ratios, but for buyers who are close financially, insurance costs absolutely matter.

[00:47:10] Tracy Hayes: I imagine you’ve had situations recently where luxury homes sat on the market for a long time, the listing expired, and then the property eventually came to you.

What’s your evaluation process when you take over a listing that didn’t sell? And can you think of a recent example where you were able to reposition a stale listing and get it sold?

[00:47:57] Craig Kincheloe: Absolutely. I actually have one right now that’s been on the market for ten months, which is crazy.

I’ll be the third agent involved.

Back between 2016 and 2020, expired and withdrawn listings were a major pillar of my business. Then the market got so hot there simply weren’t many expired listings anymore. But over the last 18 months, they’ve started coming back, so I’ve returned to that strategy.

I have a full listing audit process for expired and withdrawn listings.

For this current property — which I’m listing next week, so I won’t give too many details — one of the biggest issues was the photography.

The photos were professionally taken, but edited terribly. The mahogany floors looked bright cherry red, and homes with heavy red undertones in flooring tend to sell for less money.

The tile colors were also edited incorrectly and looked muddy brown instead of warm taupe.

Those subtle visual details matter tremendously online because buyers first fall in love with listings digitally before they ever schedule a showing.

Then when I visited the property in person, all the blinds were closed and the lighting was terrible.

The buyer’s agents aren’t going to spend fifteen minutes opening blinds and searching for light switches when they’re showing multiple homes in a row.

The house had an incredible conservation view, but you couldn’t even see it because the home wasn’t staged properly for showings.

The original agent wasn’t preparing the property before appointments — opening blinds, turning on lights, highlighting the views, and creating atmosphere.

The home was professionally staged, but it felt cold and sterile. It lacked warmth and layering. Even the lanai — one of the property’s best selling features — wasn’t staged at all.

So we’re correcting all of those things now.

Pricing was also slightly too aggressive initially, though where it sits today is actually reasonable.

On the flip side, I recently took over a $3 million listing that had sat on the market for four months. I sold it in 19 days.

What did I do differently?

I built a complete lifestyle narrative around the property.

I created a roughly 25-page “Beyond the Listing” presentation explaining what it would actually feel like to live there.

I built a custom website for the property.

I created a story around the builder and architect — their history, reputation, prior projects, and experience.

Then I created an extensive construction specifications package.

Not just finishes like countertops, appliances, and cabinetry — but what was behind the walls.

I explained how the home was over-engineered and built beyond code requirements, and then I tied every feature directly to a benefit for the buyer.

That’s sales 101 — connect every feature to an emotional or practical benefit.

Very few agents actually do that anymore.

[00:51:27] Tracy Hayes: And that extra effort matters, especially at the $3 million and $4 million price point.

You’re not just selling square footage — you’re selling craftsmanship, engineering, lifestyle, and peace of mind.

And analytical buyers probably loved all those construction details and explanations.

[00:51:59] Craig Kincheloe: Absolutely.

The builder actually appreciated it tremendously because he was a smaller luxury builder who only builds one or two homes a year. He didn’t already have that kind of presentation material built out.

That’s where my operational team really helps execute my ideas.

And once we build a successful framework, we reuse and improve it for future listings.

I’m also not trying to be the agent selling 200 homes a year.

That business model doesn’t fit my personality.

I’d rather sell a manageable number of properties while delivering exceptional service, strong results, and a truly high-end experience for my clients.

[00:52:58] Tracy Hayes: Yeah, that’s first class. You’re delivering a first-class service, and that’s why you’re thriving in markets that many agents simply don’t know how to break into.

You’re willing to go the extra mile.

That’s clearly contributed to your longevity.

You’re episode 322 of the show, so I’ve interviewed hundreds of agents, and the common denominator among the great ones is that they go beyond what’s expected.

In your market and at your price points, especially with these unique luxury homes, you have to uncover and communicate all the hidden value and benefits that matter to very specific buyers.

That’s why your story about repositioning and selling those homes so quickly is so powerful.

[00:54:08] Craig Kincheloe: Exactly.

In the luxury market, you naturally get fewer showings because there are simply fewer people who can afford those homes.

That means every showing becomes dramatically more valuable.

You have to maximize every single opportunity.

For that particular property, we only had two showings in 19 days.

One of those buyers was virtual and was planning to fly in afterward to potentially make an offer.

Transaction volume overall is down right now across almost every price range, so every showing matters more than ever.

As an agent, you have to make the absolute most of every opportunity.

[00:54:53] Tracy Hayes: Let’s shift over to luxury condos for a moment — whether it’s downtown Tampa, Channelside, or Harbor Island.

Would you describe the current condo market as a once-in-a-generation buying opportunity, or are there landmines that could turn great-looking deals into financial nightmares?

[00:55:16] Craig Kincheloe: The answer is both.

Generally, whenever there’s a great opportunity, there’s also some level of chaos involved. If you don’t know how to navigate that chaos, you can absolutely end up in a bad situation.

A lot comes down to understanding what information to review and how to properly interpret it.

Real estate agents are not trained to review structural integrity reserve studies.

We’re not trained to review milestone inspection reports, condo budgets, financial statements, or reserve funding analysis.

In my opinion, that’s a massive liability for the real estate industry.

I don’t think we’ve seen the lawsuits yet, but I believe they’re coming.

I’ve actually been working with a real estate attorney friend of mine on developing software that allows agents to upload condo documents and receive an A-through-F grading system evaluating both the structural health and financial health of a condo association.

Initially, I started analyzing some of this information manually myself, but then we began integrating AI and language models into the process.

It’s really fascinating.

There are definitely opportunities in the condo market right now, but buyers absolutely need agents who know how to navigate these complexities.

Even after clients buy properties, many still reach back out to me to review documents for them.

I was recently reviewing a condo where the buyers purchased the property below the “just market value” listed by the property appraiser — something I haven’t seen happen in years.

Normally in Tampa, homes sell for roughly 125% to 140% of just market value.

But after digging through the condo financials, I discovered that salary expenses in the association budget had increased nearly 50% from one year to the next.

So now I’m investigating that on behalf of my clients because that kind of increase raises serious questions.

You really have to dig deeply into condo financials and know the right questions to ask property management companies.

And reviewing meeting minutes is critical too.

[00:57:57] Tracy Hayes: I don’t think most buyers realize how complicated condos can be, especially first-time condo buyers.

From the lending side, we’re reviewing financial reports, insurance coverage, reserve studies, inspections, and overall project health because lenders don’t want the value collapsing after they issue the loan.

I think the software idea is brilliant — especially being able to upload budgets, meeting minutes, inspection reports, and financials into AI and have it identify risks and problem areas automatically.

That could become incredibly valuable, especially in a market with so many high-rise condos like Tampa.

[00:58:49] Craig Kincheloe: Absolutely.

We actually had to tweak the language model because initially it was giving almost every condo a bad rating.

So we adjusted it to compare buildings relative to similar properties in the area.

The next phase is creating side-by-side comparisons.

For example, if someone wants to buy on Redington Beach and there are six condo buildings available, we want the software to rank which buildings have the strongest financial health and structural integrity.

Right now, buying a condo in Florida — especially a high-rise with multiple floors and lots of units — is probably the most complex residential transaction type in the state.

[00:59:44] Tracy Hayes: Absolutely.

And from the lending side, you also need lenders who specialize in condos because many lenders don’t even want to finance Florida condos right now.

[00:59:55] Craig Kincheloe: Exactly.

There are so many layers involved.

Insurance became a major issue because deductibles in many associations were too high. Lenders became uncomfortable because if associations didn’t have enough reserves to cover deductibles after major damage, properties could fall into disrepair.

There are countless landmines that buyers simply don’t understand.

Most people are familiar with the Surfside collapse and the resulting legislation changes, but they don’t understand all the behind-the-scenes financial and structural complexities that now need to be navigated.

[01:00:38] Tracy Hayes: Another reason why buyers need someone who truly understands the condo market.

A financially weak condo association can quickly become a terrible investment.

Lawsuits, reserve issues, financing restrictions — all of that can dramatically affect values overnight.

The idea of running meeting minutes and financial documents through AI to uncover hidden issues is honestly brilliant.

All right, let’s shift gears again.

Like Jacksonville, Tampa has a huge number of buyers relocating from places like New York, DC, Chicago, and New Jersey.

When out-of-state buyers arrive excited and financially ready, what are two or three things they almost always misunderstand that you end up having to redirect them on?

[01:01:48] Craig Kincheloe: One of the biggest things is homeowners associations.

A lot of buyers from out of state initially tell me they absolutely don’t want an HOA because they’ve heard horror stories.

But once they start touring neighborhoods in their desired price range, many quickly change their minds.

In a lot of middle-class neighborhoods without HOAs, you’ll see things like cars on blocks in driveways, RVs parked in front yards, homes with tarps on roofs for years, and properties that haven’t been maintained properly.

There are exceptions, of course. In South Tampa, where I live and work, many luxury neighborhoods don’t have HOAs and are still beautifully maintained.

But in many other areas, buyers quickly realize they actually appreciate some level of community standards.

Another thing I always tell buyers is this:

If you really want to understand a neighborhood, go visit the local Publix grocery store.

I can send demographics reports all day long, but if you walk through the Publix, you’ll immediately get a feel for the people who actually live there.

I also tell buyers to drive neighborhoods at different times of the day.

And in luxury waterfront markets, there are even more details to evaluate.

For example, if a buyer is considering a waterfront home with a beautiful outdoor space, I’ll often return with them around dusk so they can experience things like mosquitoes and no-see-ums firsthand.

When someone is spending millions of dollars, the last thing you want is for them to discover after closing that they can’t comfortably enjoy their backyard because of insects.

I try to think through every little detail possible and help buyers fully understand what living there will actually feel like.

[01:04:21] Tracy Hayes: You mentioned earlier that you originally started in mortgages before real estate.

I know you’re no longer actively licensed on the mortgage side, but what advantage does that background give your buyers today, especially buyers who may not fit standard cookie-cutter financing profiles?

[01:04:58] Craig Kincheloe: I’m no longer actively licensed because I let the license expire, but I’ve always stayed close to the lending world because I understand how important it is.

The lending landscape changes constantly, so I stay connected with strong lending relationships and different loan products.

A lot of people only understand standard conventional financing, but I work with all kinds of clients and situations.

I help clients with construction-to-permanent loans, especially because I do a lot of teardown and custom-build projects.

I work with physician loans because I have many doctor clients.

I also work with self-employed buyers who sometimes need bank statement loan programs.

And of course, jumbo financing is an entirely different world as well.

Often, the best rates and programs aren’t coming from standard retail lenders.

[01:05:48] Craig Kincheloe: Asset management companies and private banking groups are often where the best lending opportunities exist.

If my clients don’t already have relationships with those institutions, I can help connect them.

Based on the type of property and loan product they need, I know which lenders are best suited for the situation and which ones are most competitive on rates.

But beyond rates, I also know which lenders actually perform — which ones can close on time, communicate properly, and execute.

That’s critically important.

I stay very involved in the financing process. Most agents simply refer clients to a lender, ask for a pre-approval letter, and step away from the process.

That’s not how I operate.

[01:06:24] Tracy Hayes: Right.

[01:06:25] Craig Kincheloe: I stay highly involved.

And I don’t only work with luxury clients.

If a past client refers me to their children or a first-time buyer, I’ll absolutely help them strategically as well.

If they need to improve credit, we’ll run credit simulations.

If they’re not ready to buy yet, we’ll put together a three-, four-, five-, or six-month action plan.

I still enjoy helping people build toward homeownership strategically.

But yes, I stay very involved in lending and financing because it’s such an important piece of the transaction.

[01:06:55] Tracy Hayes: I think that’s extremely important because simply being licensed in mortgages — just like being licensed in real estate — doesn’t truly teach you how to do the job.

Especially when you’re working with clients who earn money in unique ways.

Whether it’s understanding bank statement loans, DSCR loans, physician loans, or self-employed borrowers, you have to know where to place those clients.

You want smooth closings, so having strong lender relationships and understanding specialty loan products is incredibly valuable.

[01:07:50] Craig Kincheloe: Exactly.

There are more lenders offering physician loans now than there were a few years ago, but there are still major nuances.

Different lenders have different requirements regarding years out of residency, loan-to-value ratios, student loan calculations, underwriting flexibility, and rates.

Sometimes the lenders with the best advertised rates have the most difficult underwriting process, which can delay closings.

So there are a lot of details you need to understand to properly guide physician clients.

[01:08:24] Tracy Hayes: Right.

And for people listening, physician loans are portfolio loans. They aren’t sold on the secondary market like conventional Fannie Mae or Freddie Mac loans.

Banks offering physician loans are usually trying to build broader relationships with medical professionals — checking accounts, investments, wealth management, and so on.

That’s why finding the right banking relationship matters.

All right, this next question is very Tampa-specific.

Gas Worx connecting Ybor City to downtown is under construction. The Riverwalk expansion is happening. The Rays stadium situation is evolving. Moffitt is expanding.

Tampa’s urban core is being reshaped in real time.

For someone considering condos or urban properties in downtown Tampa, Channelside, or Ybor City, how do you frame the opportunity right now?

Is there a window here that closes before most buyers fully realize it?

[01:09:50] Craig Kincheloe: Absolutely. It’s an incredibly exciting time to be in Tampa.

The amount of development and money flowing into the city is incredible.

Downtown Tampa used to completely shut down after five o’clock. People came downtown to work, then they left.

Now you have thousands of people actually living downtown because of all the new apartment towers and condo developments.

That residential density has completely changed the environment.

Now you have restaurants, bars, retail, entertainment — an actual urban lifestyle.

And a lot of people made tremendous amounts of money by buying at the right time, especially before Water Street fully developed.

Water Street alone is a $4+ billion development surrounding the Tampa Bay Lightning arena area.

Understanding where future growth is headed is critical.

For example, the Riverwalk expansion area is personally where I’ve been investing, and some of my clients have as well.

There are also developments happening behind the scenes that most people aren’t paying attention to yet.

One example is an affordable housing project purchased by the same developer behind Armature Works.

It’s located in the closest single-family residential neighborhood to downtown and the Riverwalk.

The area is still transitional, but that’s exactly why it’s interesting from an investment standpoint.

The challenge is that the developer can’t fully redevelop the site until replacement housing is found for the existing residents due to agreements with HUD.

I’m actually using Freedom of Information Act requests to try to determine the timeline of those agreements because understanding that timeline helps me advise clients on future appreciation opportunities.

One of my favorite investment strategies is buying properties close to land value, placing tenants in them so the debt is serviced, and essentially land banking while waiting for redevelopment and appreciation.

You’re not going to find this kind of information from AI alone.

I spend a lot of time doing deep research into development patterns, city planning, and infrastructure changes so I can better predict where future appreciation is likely to occur.

[01:12:36] Tracy Hayes: Are you seeing more buyers approaching Tampa from an investment perspective now?

Not just families looking for a primary residence, but people actively asking:

“Where’s the next opportunity?”
“Where can I buy now and benefit from appreciation over the next three to five years?”

Are you seeing more strategic buyers like that?

[01:13:04] Craig Kincheloe: Yeah. At this point in my career, I’m not a huge investor-focused agent.

However, I do work with a lot of high-income earners, and with some of the more recent tax changes, real estate has become a very attractive tax strategy for many of them.

A lot of these clients are high-income W-2 earners with very few write-offs, and they’re getting crushed with taxes at 37% or higher. Their CPAs are often telling them, “You need to buy rental properties.”

So I do work with clients pursuing that strategy.

Some are simply buying rentals for long-term appreciation and passive income.

Personally — and with builders I work alongside — my preferred strategy is targeting up-and-coming urban-core neighborhoods where there’s scattered infill development happening.

I’m not talking about giant master-planned communities.

I mean older urban neighborhoods where builders are buying one home, tearing it down, and building one new luxury home in its place.

If I can buy properties in those areas now, rent them out for a few years, and hold them while the neighborhood evolves, then later I already have a pipeline of lots ready for development.

That’s the strategy I’m most interested in right now.

[01:14:31] Tracy Hayes: That really says two things.

First, it’s brilliant.

Second, it shows how much confidence your clients have in you because you’re constantly thinking ahead and trying to stay ahead of the market for them.

You’re always looking down the road — what’s happening next, what’s developing next, where the opportunities are forming.

For someone looking for a top agent in the Tampa area, that kind of forward-thinking mindset is incredibly valuable.

Now, this next question gets a little deeper.

You’ve already shared a lot of great stories, but specifically:

What do you actually say during upfront buyer conversations that helps you stand apart from average agents?

What kinds of deeper questions are you asking, and how has the increased focus on transparency changed how buyers respond to you?

[01:15:46] Craig Kincheloe: A lot of it comes down to adding tremendous value upfront.

How I approach buyers depends heavily on how they came into my world.

If they’re a referral, the process is pretty straightforward because there’s already built-in credibility and trust.

We’ll simply do a buyer consultation.

But if it’s an online lead — maybe someone from Zillow or another online source who wants to see a property — that’s a completely different process.

I don’t immediately ask them to sign a blanket buyer brokerage agreement.

I’ll do a property-specific agreement for that one showing first.

Then after the showing, I evaluate whether it feels like a good fit on both sides before moving deeper into a relationship.

Usually after the first or second showing, I’ll conduct a full buyer consultation.

I have a very consultative process that includes a detailed needs analysis and strategy discussion.

But one thing I really emphasize is fiduciary representation.

In Florida, most agents operate as transaction brokers unless they specifically establish a single-agent fiduciary relationship in writing.

Some brokerages don’t even allow agents to operate as fiduciaries anymore.

Personally, I avoid transaction brokerage whenever possible because if anything goes wrong, one side often feels like favoritism occurred.

So I explain the benefits of fiduciary representation, how I negotiate differently, and how I advocate for clients at a higher level.

Then I show proof.

One of my mentors always used to say: “Proof over promise.”

That philosophy heavily shapes how I structure consultations and presentations.

I don’t just tell people I’m good at what I do — I show them examples, case studies, negotiation wins, and stories that demonstrate it.

That’s one reason I love Zoom meetings so much.

On Zoom, I can efficiently walk clients through proof after proof after proof.

It’s much harder to do that effectively in person unless you’re carrying printed materials or complicated presentations.

Zoom allows me to visually educate buyers in a very powerful way.

[01:18:32] Tracy Hayes: That makes total sense because people are already conditioned to focus during Zoom calls from work meetings and professional settings.

When buyers hop on a Zoom consultation with you, they naturally shift into a more focused, business-oriented mindset.

You can share your screen, pull up old listings, compare photos, walk through data, and really educate them visually.

That creates a very different experience compared to a basic phone call.

[01:19:11] Craig Kincheloe: Exactly.

And there’s another huge benefit now because MLS privacy rules have changed.

I used to be able to send buyers complete copies of old sold listings with all the photos so we could compare renovations and pricing history.

Now, in many cases, buyers only see the first photo.

But on Zoom, I can pull up the listing and walk them through every photo live while explaining the differences and context.

That makes the consultation process incredibly effective.

[01:20:01] Tracy Hayes: That’s a great tip for agents listening.

Zoom isn’t just convenience — it’s a relationship-building and education tool.

You can build trust faster, communicate visually, and provide significantly more value.

And ultimately, your strategy seems to be adding so much upfront value that buyers naturally conclude:

“Craig is the obvious choice.”

[01:20:46] Craig Kincheloe: Exactly. The goal is to become the clear, logical choice.

[01:20:50] Tracy Hayes: I’ll finish with this final question.

Why do you love real estate?

[01:20:57] Craig Kincheloe: Because no deal is the same.

Every transaction is different, and every day you’re learning something new.

After every transaction, I try to debrief:

What went well?
What could we improve?

Then I evaluate my systems and processes because everyone on my team hears me say it constantly:

“We fall to the level of our systems and processes.”

Whenever something goes wrong, my first question is:

Was this a people problem — meaning someone failed to follow the process?
Or was it a process problem itself?

Either way, we fix it.

My systems are constantly evolving and improving.

But beyond that, real estate is meaningful work.

When someone buys a home, they’re buying the place where they’ll spend most of their life.

Their children grow up there.
They experience major milestones there.
They spend time with family there.
They may even go through health challenges there.

Homes become deeply connected to people’s lives.

That’s incredibly rewarding to me.

And then there’s the development side of real estate, which I’ve loved since I first entered the new-home industry at 22 years old.

My very first project started as a cow pasture.

Watching raw land evolve into streets, homes, parks, families walking dogs, kids riding bikes — seeing an entire community come to life — is incredibly fulfilling.

It’s tangible.

You can literally see the impact with your own eyes.

I have to feel meaning in my work.

If I don’t feel meaning in what I’m doing, no amount of money is ultimately going to fulfill me.

[01:23:19] Tracy Hayes: There’s no doubt from this entire conversation that you’re incredibly passionate about what you do.

That passion comes through in every story and every strategy you shared.

You genuinely want to keep getting better.

And that’s what separates top agents from average ones.

Anyone listening who’s buying or selling in the Tampa area should absolutely connect with Craig.

And honestly, agents looking to level up their careers should probably connect with him too.

Anything you’d like to leave us with, Craig?

[01:24:07] Craig Kincheloe: I really appreciate you having me on.

You asked fantastic questions that genuinely made me think about my business differently and even sparked some new ideas for me.

I appreciate the preparation and professionalism you brought to the conversation.

It made this a great experience.

[01:24:30] Tracy Hayes: Thank you. I appreciate you coming on.

I’ll send you some of the raw materials, blogs, and clips once everything is uploaded and processed.

We definitely went longer than expected, but it was a fantastic conversation.

[01:24:47] Craig Kincheloe: It really was. Everything has been first-class, so thank you again, Tracy.

[01:24:52] Tracy Hayes: Appreciate it, sir. Have a great day.

[01:25:00]

Craig Kincheloe Profile Photo

CEO

Craig is a Tampa Bay area native. Having grown up in New Port Richey and lived in South Tampa, New Tampa, Carrollwood, Brandon, West Chase, Downtown Tampa, Harbour Island, Channelside, Wesley Chapel, Tarpon Springs, and St. Petersburg. He brings a wide knowledge of almost 21 years of real estate, lending, investing, and new construction experience to the field, having ventured into the real estate world at the ripe old age of 22, bringing an education(strong background) in Business Development and Marketing. Craig, through his various real estate ventures, has had the experience of being part of over 1,000 successful residential real estate transactions before the age of 30. Craig was instrumental in the creation, branding, and selling of many new communities throughout the Bay area including Southfork, Southbay Lakes, and Churchill Bend, Craig maintains a hands-on approach with his team, from overseeing the creative and marketing efforts of the company as well as working with select, developers, builders, investors and clients. He also serves as a wealth of knowledge for agents locally and nationally.