An actual kiteboard will make it much easier to go upwind than riding a wakeboard. I know experienced kiters that ride wakeboards & can go upwind but as a beginner it's gonna be a lot harder on a wakeboard.
I have a 6m & a 12m & am waiting on my order of the new 2011 9m to come! So glad they started carrying an odd size, now I have a perfect quiver of just 3 kites!
I would definitely recommend the Grenadines! Be sure to kite Union Island as well as the Tobago Cays! Jeromie Tronet has a travel video of the area - you should check it out!
Recently in the keys kiting & jelly fish were not an issue at all. Plus it's cold so you're wearing a wetsuit anyways (or atleast I was at Christmas/New Years) but I hate being cold!
The show isn't made for kiters to watch. It's made for the other 98% of television viewers who've never heard of kiteboarding before & are amazed by just watching any kind of riding. They can't understand the riding though, so the show isn't focused on that. The producers are trying to build up how ...
NPX makes kite specific wetsuits! Also if you buy a surf wetsuit, I'd avoid the ones with the chest zip as everytime you body drag through the water with your arm out you will fill with water. Although personally I like the look of that kind of wetsuit, it is not as functional for kiting.