Florida gives real estate investors some pretty obvious reasons to hesitate. When the risks are that visible, avoiding the market altogether can feel like the safer decision.

But visible risk also gives us something useful. We can study it.

On last week’s Not Your Average Investor Show, Pablo and I sat down with Dr. Alex Stewart, founder of The Market Distillery, to look directly at three of the biggest concerns surrounding Florida real estate and Jacksonville specifically.

Alex brought the data behind each concern rather than trying to dismiss it. And that gave us a useful way to think about risk.

Let’s dive in.

The Concerns Holding Investors Back

When investors look at Florida today, three main issues consistently come up: rising insurance costs, uncertainty about where we sit in the market cycle, and questions about Jacksonville’s long-term appreciation. 

Any one of these points could easily be used as a reason to stay on the sidelines. 

So how do we understand those risks well enough to make an informed decision without pretending we know exactly what happens next?

Looking Underneath the Risk

Alex’s approach did not give us one blanket answer about whether Florida is risky. He took each concern apart and looked at the variables underneath it.

1. Insurance: It feels unstable, but that instability was driven in large part by litigation and the incentives surrounding it. Florida once accounted for roughly 75% of U.S. lawsuits against homeowners insurance companies. After the state changed the incentives surrounding those lawsuits, litigation dropped nearly in half. Since then, 21 new insurance carriers entered the state, the share of policies with government-backed Citizens fell from 21% to 2% and premium trends in the county-level data have leveled out since 2024. 

Why this matters to investors: 

The important part is not whether insurance gets cheaper. It is whether pricing becomes relatively stable. We already build about a 3% annual insurance increase into our pro formas, so seeing premiums level out matters. And when you combine that with more competition and far less dependence on Citizens, the conditions supporting that stability look much healthier than they did a few years ago.

👉 Is Florida Insurance Still a Reason to Avoid Real Estate? 

2. Market Cycle: A housing slowdown can look like the start of a crash, but Alex uses transaction volume as an early signal because sales can begin changing before prices fully respond. After an all-out sprint in 2020–2021, Jacksonville spent three years treading water to catch its breath. 2026 is the first year in this adjustment where sales and prices have both shown growth. The year is not finished, but Alex sees that combination as evidence that Jacksonville may be turning the corner.

Why this matters to investors: 

One thing this framework makes clearer is that a real estate cycle does not have to include a major drop in home prices. Historically, these cycles are more often periods of faster growth and slower growth. Looking at sales alongside prices gives us another way to understand where Jacksonville may be in that cycle without assuming every slowdown has to end like 2008.

👉 Is Jacksonville Real Estate Turning the Corner? 

3. Appreciation: Future upside feels uncertain if you rely on a single forecast, but modeling a range of historical outcomes brings clarity. Across 47 years of Jacksonville data, the worst 13-year period finished about 5% above its starting value, while the best finished about 170% higher – with zero 13-year periods ending in the red.

Why this matters to investors: 

This is why I keep coming back to the holding period. We think of a full market cycle as roughly 10 to 20 years, and Alex’s chart makes the reason easy to see. The shorter the hold, the more uncertainty there is around appreciation. As the holding period gets longer, that historical range changes dramatically. That is why I described buying and holding through a full market cycle on the show as the greatest risk mitigator for getting the timing wrong. 

This reframes our whole decision-making process. The investor moves away from asking, “Can something go wrong?” and starts asking, “What is most probable, what could go wrong, and can my investment handle it if it does?” 

👉 What 47 Years of Jacksonville Data Says About Holding Period

NOT YOUR AVERAGE INSIGHT: Make Uncertainty Underwritable

👉 The Better Question to Ask When Real Estate Feels Uncertain

The goal is not to eliminate uncertainty. It is to make uncertainty easier to underwrite.

You can spend all day asking “what if?”

There will always be another scenario.

Another downturn.
Another expense.
Another event nobody predicted.

Eventually, asking what could possibly happen stops helping.

Alex’s suggestion was to start with what is most probable, then use the numbers to understand the range around that expectation.

That is exactly what we did with these three Florida concerns.

• Insurance risk became easier to understand when we looked at litigation, carrier participation, Citizens exposure, and premium trends.
• Market cycle risk became clearer when we looked at the relationship between sales and prices.
• Appreciation risk became more useful when we stopped looking for one forecast and started looking at the historical range across different holding periods.

A market with clearly identifiable risks can sometimes be easier to evaluate because you know which variables deserve your attention.

There will never be a market where nothing can go wrong.

The more useful goal is understanding the market well enough that uncertainty does not automatically become a reason to avoid it.

And for me, that is the most valuable part of Alex’s framework. It gives us a way to respect the risk without letting the existence of risk make the decision for us.

Just remember… Don’t Be Average.
Gregg Cohen
Co-Founder, JWB Real Estate Capital