Hi I can't answer the travel questions, but as for riding, you are in for a treat. Forget clearwater beach... drive down to the sunshine skyway or Ft. Desoto Beach (about 20 minutes). We get a lot of easterly winds this time of year and it's all flat shallow water. Later as the fronts come through, it switches to westerly and we can ride the waves on the gulf beaches.

Typically the wind range here is 15-25... occasionally 30-35 (but not regularly). I would pack the 14 and a 12.

Check out some videos of East Beach here:
http://www.floridakiteboarder.com