1 & 2 you should have no problem with. 3,4 & 5 you may have a problem with. The folks at Suncoast were very friendly when I was there. Some very cheap accommodation available at a motel on a boat dock right on Clearwater Beach through SFS.
The weather is just right for practice flying IFR in thunderstorms if that's what you like! Fraid it's generally very hot, humid with plenty of towering cumulus in the afternoons. Mornings generally the best.