Simple question Craig, tricky answer. Florida is larger than 60% of the countries on earth, it is a big place with varied conditions. Any preference on where in the state you would like to go? Traditionally wind conditions vary dramatically with the time of year. Normal weather patterns have been elusive this year, lots of westerly wind, cooler temperatures and little normal clocking of winds with frontal passage. Typically our best winds come through between December and March perhaps April in some years. This year, in the SE anyway, not so much unfortunately.
You should look over the three stickies on kiting in Florida for some more ideas and background at:
http://fksa.org/forumdisplay.php?f=89
As a rule, it is hard to find more than a kiteboard to rent in Florida unless you sign up for a class or sea taxi run with some providers. Best to bring your own gear if you can.
Regarding squalls, they really are fairly easily avoided, but we have to think a little bit and try. Some ideas along those lines appear at:
http://fksa.org/showthread.php?t=69