Ok so I don't live there, but my folks do. They have a place that they spend 6 months out of the year at.
They come home from April to June, and then from Sept-Dec, and stay in sunny Fl the rest of the time.
They started by going and renting a place for a few weeks, then a month, then 2 months, and finally they leased to purchase a year, and then bought their current place.
We have also stayed in condo's in Estero. While the Condo was awesome, on a golf course community, and huge, with lots to do, I found it too far from any beaches. Took at least 20 minutes by car to get to any beach, and longer to get to the "good ones".
I think you need to consider what your habits are, what your past times are, and how much time you want to spend on/in the water.
I like my folks place it's in a retirement community the "houses" are basically trailers with add ons. They have a lenai and a deck that are as big as the actual house. They are also on the canals so they can go to the beach via boat or car, or bike. They are on Fort Myers island proper. They hang out at Love Key a lot. They are water people though, love to be in it, fish, swim, play etc. My dad fishes year round. The community is very active with a social events several evenings a week, and dances, and several of their close friends have places there as well. They also have bike/golf cart paths, so they can exercise, and be out and about as much or as little as they want.
There was an issue with insuring the place though due to hurricanes and FEMA rules it's only insurable only up to a point, which from what I understand makes it impossible to replace the structure should a hurricane hit it.
I would think you need a long vacation to the area, and many trips leading up to it, perhaps staying in each type of community to get a feel for it.