A long time ago in a galaxy far far away, my grandparents moved to Fort Meyers. They had only visited Florida before that. They had good friends who had moved to Florida and raved about how great it was. My grandparents sold their house in a cold weather part of the country and bought a nice home in a 55+ community with a screened-in pool in the backyard + a canal in back with a small boat dock.
18 months later, they put the house back on the market and moved back to their original cold weather state. They learned that my grandmother hated to sweat. Hated all the bugs. Hated the hot weather for most of the year. Hated being in a 55+ community where she felt everybody was complaining and, as she put it, "everybody is OLD here!"
I think that
@HopperFan's suggestions are good ones. Living somewhere and vacationing there can be very different. Also, just something to consider, but often a home/condo/townhouse in a 55+ community can be harder to sell later on because your potential market of buyers is ONLY people who are 55 and older. Thus, the total # of potential buyers is less than in a non-age-restricted community.