Not Your Average Investor Show

Where is Jacksonville’s real estate market now, and where could it be going next?

National headlines do not always reflect what is happening in Jacksonville. In this Q4 Jacksonville Real Estate Market Outlook, Gregg and Pablo will break down the latest local housing, rental, and property management data.

They’ll examine what has changed since last quarter, what the current numbers say about Jacksonville, and what investors should watch heading into Q1 2027.

They’ll cover:
- Home prices and appreciation trends
- Housing inventory and days on market
- Foreclosures, interest rates, and financing conditions
- Rent growth and rental demand
- Occupancy, lease renewals, and resident stays
- Property turns, maintenance, and management trends
- The signals that could shape the next quarter

Are Jacksonville prices holding up better than expected? Is rental demand changing? And do current conditions point to more risk or more opportunity for long-term investors?

Listen NOW!

Chapters:
00:00 Welcome and Setup
01:57 Show Format and Disclaimer
03:03 Jacksonville Sales Snapshot
04:17 Inventory and Foreclosure Reality
09:52 Why Foreclosures Stay Low
12:33 Normalization Price History
15:49 Rent Market and JWB Portfolio
18:56 Workforce Housing Advantage
21:42 Rates vs Prices Deep Dive
28:32 Demand Drivers Migration and Life Events
34:11 Supply Squeeze Lock In and Builders
37:23 Supply Crunch Prices Up
37:34 Builders Falling Behind
39:37 Inventory Keeps Dropping
40:40 Sales Rising Despite Rates
42:38 Jacksonville Market Wrap
44:50 Coil Effect Explained
46:29 Rate Drop Cycle Data
49:10 Why Buy Now Incentives
51:41 Downtown Revitalization Trigger
53:05 10K Residents Flywheel
55:10 Austin Tampa Nashville Deep Dive
58:42 Extra Appreciation Math
01:02:05 Predictions Scorecard
01:05:06 Client Wins and Proof
01:07:08 Q&A Hurricanes Evictions ARMs
01:15:00 Closing & Next Episode

Stay connected to us! 

Join our real estate investor community LIVE: 
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Schedule a Turnkey strategy call: 
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Subscribe to our channel  @notyouraverageinvestor  
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🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Buying a rental property without knowing how to check the market data yourself may mean trusting assumptions you’ve never verified.

On this Not Your Average Investor Show, Pablo and Gregg break down three free tools every rental property investor can use to research a market for themselves without expensive software or relying entirely on someone else's assumptions.

They’ll break down:
🏠 Current home prices with Redfin: What are homes actually selling for today, and how does the market compare nationally?
📈 Home price appreciation with FHFA: How has the market performed over the long term, and does the appreciation assumption you're using have historical support?
💰 Rent prices and rent growth with Zillow: What are homes renting for today, and how have rents changed over time?

If you're evaluating a new rental market, reviewing a pro forma, or simply want to become a more informed investor, these are three tools you'll want to know how to use.

Listen NOW!

Chapters:
02:24 Quarterly Market Events
04:26 Jacksonville Boom Town Data
06:06 Downtown Revitalization Thesis
10:17 Why Appreciation Beats Cash Flow
11:55 JWB Cares Golf Recap
13:32 Free Tools Overview
14:37 Why Redfin Not Zillow
17:08 Redfin Data Center Walkthrough
22:13 Reading The Excel Report
26:16 Avoiding Seasonality Traps
29:35 Interpreting Market Speed Signals
29:58 Redfin Data Reality Check
30:45 US Report Benchmarking
32:40 Cash Flow First Framework
34:03 Inventory Signals Using Redfin
36:46 FHFA HPI Tool Walkthrough
39:40 Normalize Appreciation Rates
42:30 CAGR Calculator Method
46:23 National HPI Baseline
48:32 Zillow Rent Data Setup
54:29 Rent Growth Discounting
57:24 Community Wrap Up

Stay connected to us! 

Join our real estate investor community LIVE: 
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Subscribe to our channel  @notyouraverageinvestor  
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🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
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Sitting on a rental property with a mortgage rate around 4% may be holding you back from asking the most important question...

"What's the best financial outcome I can create?"

On this next Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez break down a real portfolio decision Gregg recently modeled for a longtime JWB client with roughly $2 million in equity.

Does it make sense to keep several sub-4% mortgages in place, or refinance at a higher rate, unlock equity, and use it to buy more rental properties?

They’ll break down:
✅ Why a low mortgage rate shouldn’t be evaluated by itself
✅ How Gregg compared keeping the existing loans versus refinancing and buying more properties
✅ Why the higher-rate strategy projected nearly $1 million more over 10 years in this specific client scenario
✅ How an investor’s timeline can change whether unlocking equity makes sense

If you’ve built significant equity in your rental properties but aren’t sure whether you should leave it alone or put it back to work, this episode will give you a better framework for thinking through the decision.

Listen NOW!

Chapters:
00:00 Beware Rate Trap
01:33 Show Welcome Banter
02:18 Justine Rent Update
05:22 Quarterly JAX Events
09:11 Dormant Equity Explained
16:22 Mortgage Rate Trap Setup
18:56 Client Case Study Intro
20:43 Portfolio Returns Breakdown
22:22 Equity Snapshot Reality
29:12 Refi Plan Framework
35:25 Equity Pull Decision
36:43 Risk And Cash Flow
37:24 Running It Back
39:18 Redeployment Plan
41:36 Year One Snapshot
42:50 Reserves And Tradeoffs
46:40 Ten-Year Outcome
50:46 Rates And Retirement
52:50 Scenario Planning Tools
56:01 Q And A Financing
01:01:11 Rentals For Stability
01:04:59 Next Week And Wrap

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Thinking about house flipping or passive rental investing?

One can help you build capital faster. The other can help you build wealth without adding another job to your life. But do you really have to choose just one?

On this Not Your Average Investor Show, Gregg sits down with JWB investor Justine Herrera, who has experienced both sides of real estate investing. She completed three successful flips before using that capital to buy her first long-term JWB rental and she still sees a place for both strategies.

They’ll break down:
✅ How active and passive real estate can work together
✅ When flipping can help fund a long-term rental strategy
✅ How to own rentals without creating another job for yourself
✅ Why the highest possible rent may not always be the best financial decision
✅ How to build a real estate strategy around your long-term goals

They’ll also look at a real decision from Justine’s JWB property: Should you accept lower rent to keep a good resident or hold out for more and risk vacancy and turn costs?

Gregg will break down the numbers so you can see why “prioritizing occupancy” can sometimes be the smarter move.

Listen NOW!

Chapters:
00:00 Meet Justine Herrera
02:22 Quarterly Market Outlook
03:35 Justine’s Real Estate Why
06:42 From Flips to Turnkey
07:44 Renewal Win Win Story
10:02 Property Management Reality
14:44 Helping Friends Invest
22:32 Active vs Passive Strategy
24:58 Flipping Risks Today
28:19 Active Funds Passive Goals
29:08 Solo Flipping Stress
29:42 Finding a True Partner
30:20 Flips to Passive Wealth
31:52 Justine Numbers Disclaimer
33:08 First Turnkey Purchase
34:00 Why This One Worked
35:47 Year One Performance
37:40 Incentives Boost Cashflow
38:47 Pac Man Principle Explained
40:20 Reverse Pac Man Market
44:56 Rent Comps Q and A
48:35 Justine Advice and Next Steps
53:06 Community Wrap and Call
54:32 Next Week Rate Trap
55:02 Final Sign Off

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

There are plenty of reasons investors may feel cautious about Florida real estate right now. Insurance costs went up. Home prices hit all-time highs. And the 2023–2025 slowdown has people asking if we are seeing the beginnings of a major correction. 

On this Not Your Average Investor Show, Gregg and Pablo are joined by Dr. Alex Stewart of The Market Distillery to look at those concerns through the data. 

Dr. Alex will share parts of his market analysis, then Gregg and Pablo will dig into what they could mean for long-term rental property investors.
 
They’ll break down:
✅ Why Florida insurance costs went up and what the data says now
✅ Jacksonville’s worst-case vs. best-case home price appreciation over time
✅ Whether 2023–2025 is a sign of things to come, or a part of the cycle
✅ And more!

If you’re asking whether today’s headlines are reasons to stay away from Florida real estate, this conversation will help you look past the headline and understand what the data is actually showing. 

Listen NOW!

Chapters:
00:00 Florida Myths Setup
01:40 Introducing Dr Alex
02:58 Origin Story Market Distillery
03:57 Why Independent Market Data
07:59 JWB Connection And Education
13:28 Florida Insurance Reality Check
14:56 Litigation And Carrier Comeback
19:01 Premiums Stabilizing In Florida
25:56 Market Cycle Crash Talk
28:06 Fear Headlines And Investor Psychology
31:55 2008 Vs Today Correction Data
36:21 Modern Housing Cycle Framework
37:16 Market Cycle Framework
38:15 Testing the Model 2004-2012
40:45 Signals Sales vs Prices
41:18 Post-2014 Cycle to 2026
43:26 What Should You Do
44:09 Months of Inventory Link
47:52 Buy and Hold Strategy
49:26 Time in Market Proof
50:47 Risk Odds and 13 Years
53:19 Upside vs Downside Visual
56:01 Money Supply Cheat Code
58:54 Personal Investing Moves
01:01:11 Black Swan and Fear
01:05:24 Optimism Investing Mindset
01:06:47 Wrap Up and Next Episode

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Data came out saying Florida renters need about $77,500 a year to afford a modest two-bedroom rental.

That sounds like bad news for Florida real estate investors. But is it really? Jacksonville, Miami, Tampa, Orlando, and South Florida all tell very different stories when you compare rents, prices, and investment economics.

After signaling a potential rate increase in September, rates dropped in August. Should investors wait, or act now while options like JWB’s 3.9% financing are still available?

These are the topics that JWB's cofounder, Gregg Cohen, and host, Pablo Gonzalez will tackle on this week's edition of the Not Your Average Investor Show.

They’ll break down:
✅ What the $77,500 Florida renter number is really signaling
✅ Why Jacksonville may not move like Miami, Tampa, Orlando, or South Florida
✅ Why rates dropped when a possible September rate hike was what was predicted
✅ How JWB’s limited 3.9% financing offer could change the math on a rental property today

What does it all actually mean for investors right now? And is waiting the smarter move… or the riskier one? 

Listen NOW!

Chapters:
00:00 Florida Rent Shock
02:04 Renters Boost Credit
03:34 How Rent Reporting Works
05:26 Affordable Housing Groundbreaking
05:51 LIHTC Explained
08:00 Why This Deal Matters
11:02 JWB Cares Fundraising Update
12:05 Is Florida Unaffordable?
14:16 Florida Markets Compared
17:09 Jacksonville Rent Advantage
18:39 Income vs Rent Burden
24:53 Home Prices and Cost of Living
26:22 Miami Cost Shock
26:44 Population Growth Runway
30:21 Jacksonville Bubble Explained
31:55 Separating Headlines From Data
34:14 Why Big Markets Only
36:00 Fed Dot Plot Reset
38:52 Rate Probabilities Whiplash
41:43 Stop Sitting On Sidelines
43:58 Boring Buy And Hold Wins
46:16 Deal Breakdown Ottawa Avenue
50:54 Wrap Up Community Q And A

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

A rental property pro forma can show cash flow, appreciation, tax savings, and long-term profit. But only if you know where to look and what the numbers actually mean.

On this Not Your Average Investor Show, Gregg and Pablo break down how to read a rental property pro forma through the five profit centers. They’ll explain why some returns show up in year one while others build over time, where tax savings fit into the projection, and how investors can use the numbers to make a better buying decision.

They’ll break down:
✅ How to tell where a rental property’s returns are actually coming from
✅ Which numbers matter now versus what builds over time
✅ Where the five profit centers show up on a pro forma
✅ What to look for on a deal sheet before making a buying decision 

Knowing where the returns come from, when they happen, and which assumptions drive them can help you evaluate a rental property more clearly.

Listen NOW!

Chapters:
00:00 Why Pro Formas Matter
01:56 Five Million Distributed
04:08 Rental Market Strength
06:52 Webinar Dates Announced
08:40 Meetup Shoutout
10:44 Juiced Pro Forma Example
13:24 Cap Rate and NOI Basics
15:01 Seven Pro Forma Red Flags
19:07 Appreciation and Reserves Scam
24:48 Selling Costs Reality Check
26:27 Using AI to Audit Numbers
30:20 Recasting to Real Returns
33:00 JWB Pro Forma Preview
33:35 Unlocking 3.99% Loans
34:59 Deal Sheet Overview
37:29 Assumptions Behind Returns
43:19 Vacancy Turn Timing
49:24 Cashflow Swings Reserves
51:31 Tax Savings Done Right
01:00:49 Audience Q&A Rapid Fire
01:11:08 Wrap Up Next Week

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Trump Accounts have created a new way to set your family up for a solid financial future at a time when 401(k)s are reaching record highs.

But have you ever asked yourself this: If your kids inherited it tomorrow, would they know what to do with it?

In this week's Not Your Average Investor Show, Gregg and Pablo discuss retirement, 401(k)s, Trump Accounts, and what it really means to leave wealth to the next generation.

They’ll break down:
✅ How Trump Accounts don't just help children invest earlier, but also teach a valuable lesson
✅ Why people can have a large 401(k) and still feel unsure about retirement
✅ What your kids actually inherit when they inherit rental properties

Leaving your children assets is one thing. Leaving them with the knowledge and confidence to make good decisions is another.

Listen NOW!

Chapters:
00:00 Hot Topic Preview
02:00 HomeStep Fundraiser Win
05:09 JWB Property Management Ranking
07:21 What Are Trump Accounts
09:43 Why Compounding Matters
12:43 Community Gifting Mindset
18:54 Case Study Numbers Breakdown
21:50 From $5K to $500K Future
24:16 Retirement Reality Check Setup
24:27 Retirement Confidence Paradox
25:11 Vanguard Data Bright Spots
26:06 Auto Enrollment and Autopilot Investing
27:32 Hardship Withdrawals Surge
30:01 Gallup Poll Confidence Drop
31:11 Why the Model Feels Broken
32:43 Education and Community Fix
34:45 Passing Rentals to Heirs
38:32 Step Up Basis Explained
42:03 Next Episode and Closing

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

The housing bill passed. But will it actually lead to more homes in Jacksonville?

That is the part no headline can answer yet.

In this week's Not Your Average Investor Show, Gregg and Pablo are breaking down what made it into the final law, including manufactured housing, office-to-apartment conversions, renovation programs, zoning reform, and the 350-home provision.

They’ll walk through the bill through JWB’s operational lens, explaining which ideas could realistically work, what could stand in the way, and what it would take for experienced builders to bring them to market.

You’ll learn:
✅ Will any of this actually increase housing supply?
✅ Could manufactured housing make homes cheaper and faster to build?
✅ Why does density matter so much?
✅ And how much depends on what local governments decide to allow?

The law may create new opportunities, but it does not build homes on its own.

Listen NOW!

Chapters:
00:00 Housing Bill Headlines
01:37 Welcome Home Fund Mission
02:45 How the Fund Works
06:56 Donation Levels Perks
08:02 Golf Tournament Access
11:00 Live Ticker and Roll Call
14:35 Bill Overview: Supply Reforms
19:08 Key Provisions Breakdown
20:24 Institutional Investor Rules
23:56 Exceptions Build Renovate
27:34 Qualified Homeownership Programs
28:45 Fundraiser Momentum
29:09 Institutions As Partners
33:11 Local Zoning Reality
36:35 Nimbyism Explained
41:15 Modular Housing Shift
49:43 JWB Experiments Lessons
52:42 Homeownership Incentives
54:32 Community Giving Rollcall
58:08 Bill Takeaways Wrap
59:50 Next Week Preview

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

It is too easy to fudge a rental property deal sheet, sell the property to an investor, and blame the property manager when the property doesn't perform as expected.

But the person that loses most in that scenario is the investor!  

That's why we'll be breaking down real deal sheets in this week's Not Your Average Investor Show!

JWB Co-Founder Gregg Cohen and host Pablo Gonzalez are breaking down a Memphis rental property deal and comparing it with how JWB looks at rental opportunities in Jacksonville.

They’ll walk through the numbers, point out what may or may not be included, and show you why monthly cash flow is only one part of the picture.

You’ll learn:
✅ How to compare rental property deals across two different markets
✅ Why two deal sheets may show expenses differently
✅ Which numbers and assumptions deserve a closer look
✅ How financing and property management can affect the deal
✅ Why the biggest cash flow number does not always tell the whole story 

A good deal is not just about the city or the biggest number on the page.

Listen NOW!

Chapters:
00:00 Deal Sheet Showdown
02:04 Resident Testimonial Story
03:51 Why Great PM Matters
07:24 Show Origin and Disclaimers
08:17 Seven Pro Forma Red Flags
13:38 Memphis Deal Sheet Overview
15:00 New Construction Appreciation Trick
18:23 Rent Growth and PM Fee Incentives
24:12 Cash Flow Table and Lease Assumptions
28:14 Renewals vs Turnover Maintenance Reality
31:22 Maintenance Reality Check
32:30 2.5% Assumption Exposed
34:30 Vacancy and Management Fees
36:01 Occupancy and Renewals Matter
37:06 Tax Savings Math Errors
39:11 Property Tax Fact Checking
40:48 Loan Payoff Confusion
43:05 Appreciation and Selling Costs
48:39 Right Sizing the Pro Forma
50:35 Memphis vs Jacksonville Returns
53:22 Equity Harvesting Strategy
56:11 JWB Pro Forma Q&A
01:02:58 Jacksonville Downtown Catalyst
01:05:54 Community Wrap Up

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies