Danimal,
I came from a long wakeboarding history too. You'll definitely need a light wind board for around here. Good light wind boards have very little rocker and are typically pretty wide. For your high wind board you can actually use your regular wakeboard, if you want to save money, despite what people say. I did for years. Eventually you'll probably want to get something with a little more flex though, as I finally did. We're frequently riding chop while kiteboarding and the flex helps smooth the ride and also acts to give you more rocker at the times you need it while still being able to go upwind good. Lots of rocker = slow and not good upwind. With enough wind though... basically anything works.
On to bindings... Most people ride straps, but if you're anything like me you'll want to switch to wakeboard bindings as soon as you can go upwind consistently. Till then, for safety, stick with straps.
It's a great time to start. This is the first year that the equipment has started allowing me to ride the way I really want to.... lots of unhooked stuff and not afraid to drop the bar... just like wakeboarding. It's helped me alot. You'll be amazed at how quick the tricks come over. I've learned a lot this year, some of the tricks comes over on the first try and there's still quite a few I haven't even tried yet. And in the waves... Oh man... you can't buy boat wakes that big!
Have fun!
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