Yes to these 2!!!
--Are tire covers worth the cost?
--Should I check the caulking more often in SW Florida?
I was in Florida Keys when hurricane Irene was blowing through the Florida Straights. Plan B was to head to Naples and put the trailer in an enclosed storage facility there (which I cant remember the name of right now) but it was not too outrageous in price. Maybe do a search for indoor RV storage Naples Fla
FYI Plan A was to hang out and watch Irene head north