There are plenty of great instructors in this area. I took my lessons from Randy Radcliffe. He's a great guy/instructor. Also, the Eckerd College guys teach down here at the St Pete Beach area. Probably the best choice for you since you're going to be driving quite a distance and coming to Indian Rocks Beach, is to get your lessons from Watersports West(
www.watersportswest.com). They're right there, and they do I believe most of their lessons at Three Rooker Bar which is a little closer drive for you. They're all great guys out there, and just like most of the other instructors in this area, stress safety. If you don't want to go to WSW for some reason, I can post Randy's number, he's a PASA certified instructor. Randy teaches at the Skyway usually which would be a long hike for you.
As far as DVD's good idea, totally forgot about that. I watched all the videos and read all the magazines. As for flying a trainer kite, I think its debatable. I had fun with mine and it allowed me to be sure I wanted to spend the money on lessons, but as far as making the lessons easier, I don't think it made any difference. Most instructors want you to put time in on a trainer, and I did, but think I would have been the same if I never touched a trainer. There's actually a thread about this on kiteforum right now.
Hope that helps