Where do you live and where do you plan on riding? What kind of riding are you planning on doing the most, wake, big air, waves? While all kites will do all styles, some are are more suited for a particular style than others.
I would buy the cheapest stuff you can find, and learn on em. You are going to beat them up learning. Once you get going on it, then buy some nicer ones.
Thats about right for 05 kites in good condition. Prob some similar deals out there fro some 06's as well.
www.iwindsurf.com is where to find the used stuff. Also check
www.bestkiteboarding.com. They usually have a really good used selection that you will know isnt torn up or have twisted bladders.
I would use that big board to learn on, then dump it. A wakeboard works but requires alot of power because of the rocker.
hey Ryan, have you ridden a Waroo yet? Rode one for the first time Sat, and not sure if I want to pull the trigger on one. The power and speed was impressive, but a beating with no stopper ball. I hear the newer ones have a stopper.