You could start out with a cheaper flat deck or something. But just know that a few of the companies out there really don't give their lower end boards the time and attention they deserve. These boards really aren't constructed that well, and they may be more trouble than they're worth. That's just something to think about. I wish it wasn't that way, because right now, a flat deck is a super affordable way for someone to decide if they like wakeskating or not, but it may also ruin their experience if they have some
board that falls apart on their family trip or something.
250.00 can be a big commitment if you're not ready. You could check out ebay to see if there's a cheap board that you wouldnt' mind dropping the $$ on to test out the waters. Otherwise, if you do buy a high end skate, there will be a re-sale value that will vary, depending on demand at various seasons, etc.
I do feel like mentioning that oak makes a very nice wood concave (PBT base) and you don't have to spend 250.00 on it. Sattelytes are a tad more expensive (I'm not sure why) but I rode one and again, it's a super solid deck. Just know that you can buy a wood board from one of these two companies at a reasonable price and you don't have to worry about them falling apart.
Finally, just know that an integrity is going to feel different than a wood board. They're lighter, less dense boards. Some people like that, others think they're too light. One other factor is that if you like the idea of shaping your own rails, you can do that on an integrity. I'm not sure on the oak weights any more becuase i haven't held one since expo, but sattelytes have a nice weight to them, the ride nicely...and personally, i don't want to have to deal with any rail shaping. but one thing is that with all three of those boards, you're definitely going to get something solid that will lastfor a while.
Anyway, I'm pretty sure sattelyte sold out of their first batch of boards, but the oaks just shipped: http://www.boardstop.com/index.php?cPath=22_149&osCsid=jak4fvr2abpop5ss5jq5 qfn3f2