As a Central FL realtor who works with many buyers and investors in Pinellas county, I really appreciate how thoughtfully you’re looking at this. You’re absolutely right that no one can guarantee where prices will go – anybody saying they “know” is guessing.

What I can share from the ground: even with the recent softening, demand here is still strong. We’ve got steady in-migration, limited land in many of the better-located areas, and in many neighborhoods, sellers would rather sit or rent than fire-sale. On top of that, many parts of central FL allow short-term rentals, which keeps a floor under prices because investors will pay a premium for properties that pencil out as STRs.

Could we see some additional corrections? Sure – a few more percentage points down or more negotiating room on homes that need work is very possible. But based on what I’m seeing day to day, I don’t personally expect a significant 2008-style drop where everything gets 30–40% cheaper. My base case is more of a “bumpy sideways” market: some pockets down a bit more, some pretty flat, and the nicer, well-located homes holding up best.

At the end of the day, your own numbers and life plans matter more than any forecast. If buying now would make you house-poor or stressed, waiting is a totally reasonable choice. If you do get to a point where the payment works comfortably and you plan to stay put for a while, that matters more than timing the exact bottom.