Do you by chance have any experience with Jacksonville or that area...again for liveaboard marinas, schools and airports?
I don't have experience with the Jacksonville area, but I do know there are a lot of liveaboard marina options there. It's a big city so there should be some decent education options.
I've lived in Florida for 11-12 years(3 aboard). Did 7 years in the SE area(Fort Lauderdale) and don't
recommend that area at all. Did a few years in Orlando and I do recommend that town for family life. It's not touristy if you stay out of the SW part of town.
I've spent some time in the Tampa area and it's a decent city. Lot's of sailing opportunities, but traffic is a real consideration there. The entire east coast of Florida also has a ton of very small marinas, St Augustine all the way down to Stuart. The towns all tend to be small and tend to flip flop from being nice to being pretty shoddy.
Ft Myers isn't a bad area at all, though it tends to be a little more old people than the rest of the state. The marina I was at down there wasn't a liveaboard marina, but there's a Marinatown in Ft Myers that has very affordable liveaboard rates that seemed to be nice. The Ft Myers area has a lot of little marinas and a beautiful amount of cruising, so it's not a bad area at all to base out of while you look.