I don't have all the answers, but I am happy to read and learn from others.
I may not retire to Florida, but it could happen. Here's somethings I have learned.
DO NOT HAVE A POOL. You are right about the cost, and most retired folk rarely use their own pool. The park has a great pool, and most retired people wouldn't go there either.
Air conditioning- I need to learn to do without wherever I retire. Air conditioning is great for a few months a year, perhaps as much as half the year, but the rest of the time, I have to learn to accept the temperature and humidity. I know the Gulf coast is not so bad most of the year as far south as Tampa, but it's still a wee bit cold in the winter. Jackets in the house can deal with much of that. I might retire to the Virgin Islands where I already know I can tolerate the weather without AC for 3 out of 4 seasons. The humidity is not too bad and the weather is milder. But there's those pesky hurricanes to deal with. Weather, heating and cooling costs are tough no matter where you go.
While I am not a big fan of condos, I might consider just accepting the fees that come with them and skip all the fighting against roof problems, fire ant problems, etc. Sure, they have to be dealt with, but it would just be part of the built-in costs.