Since I (we) just did what you are contemplating I’m going to throw in my 2 cents worth. After “researching” the area from Venice (where my mother lives) to the south end of Pine Island (where my grandfather lived), for about 15 years, we retired from central Ohio to Burnt Store isles, in Punta Gorda, this year.
Over those years we made trips to the area as often as possible and after looking at many, many locations decided on a couple of neighborhoods that we liked. My main goal was to be on sailboat access water and my wife wanted a pool, other than that we kept our requirements reasonable for our budget. We then hooked up with a buyer’s agent here a couple of years ago and began the process of elimination, as everything was a bit of a compromise. We ultimately found a home that had been purchased, redone and rented, at least seasonally, that the owners (who also lived in the neighborhood) decided to sell. Even though the timing was not perfect, everything else was as good as we felt it would get and we were fortunate enough to be able to buy it. Since we had about a year before we could retire, we contracted with the same real estate company the previous owner had and rented it over the winter of 2012/2013, which really helped with the expense of owning two homes.
The main compromise (boating-wise) for our home’s location is that it takes about 45 minutes to travel through the canals and Alligator creek to get into Charlotte harbor. I am between sailboats as I sold the one I had in Ohio before moving and have purchased a “fishing” boat to explore and get the “lay-of-the-land” while researching for my next sailboat. We live on a nice wide canal and one of the neighbors has a Hunter (see picture) that I think is about a 40 footer and I know he has to time his transitions to Charlotte harbor with the tides. The depth of these canals I found is about 7-12 feet in most places in our area. There is a pinch point getting to the north fork of Alligator Creek, which used to be a lock but is no longer and a project is in the works to widen it from approximately 17 feet to 21 feet which will make it much easier to transition for the larger “beamier” boats.
Personally familiarizing yourself with the area is the only real way to answer questions to your satisfaction. As was mentioned above, don’t just take someone’s word for it that the home has “sailboat access”. A lot of the neighborhoods here have associations and boating clubs with newsletters that you can access from the web and will help you in getting the whole picture but seeing first hand is best. In our area, it looks to me like about 99.9 % of power boaters keep their boats on a lift and about 50 % of sail boaters do. Also, in “the neighborhood” there are two Beneteau 331’s and a 370 (see picture) that are on lifts. My preference is to not leave the boat in the water all year, hence I’m having a lift installed. Yes, it is hot and humid in the summer but with AC, the pool and being on the water (usually a breeze), I gladly take the sunshine almost every day and very moderate temperatures throughout winter (check the current temperature map of US) for a few really hot months, especially, after those mid-western winter months I suffered through.
Good luck with your search, coincidentally, I have a daughter that lives down the road from you in Tumwater. PM me if you want for further information. Now, if I could just hook up with one of the sail boaters here that needs a crew sometime until my next ship comes in …. J