Our member wildernesstech
keeps a boat in Missouri as well as in the Caribbean.
Sailing the ocean is actually easier than sailing fresh water--for example, the great lakes. Salt water is more buoyant for one thing and often lakes have shallows with high winds--that means steep waves/chop. Some large bays have the same issues, too.
There's no hurry to purchase real estate in Florida's down market is there? You might consider renting a slip in a marina for your visits there so that you won't be "stuck" with a bit of property that you don't want or need later. It would likely be just as easy, cheap, and more fun to keep your boat in the Caribbean than in So.Fl.