If it was me, I would get a modest house/apartment in Florida, then get a fast, trailerable boat you can explore with, go to the Bahamas if you want, etc. Then put it on a trailer when you are done cruising. Less maintenance, less worry.
A big issue for me, if I was a live aboard, would be the threat of hurricanes. It was stressful enough trying to get my boat out of harms way the past few weeks, but if the boat was also my house that would have been double stressful.