new vs. used

I'm trying to find a good first wakeboarding boat. I know more or less the type of features I want (direct drive, tower, open bow) but I am unsure of what he best deals are and where to find them. If I go used I'd look to spend 20K or less.

My question is, would it be better to look for a good used boat in this price range? Or would I be better off, buying a new boat, which would be quite a bit more expensive, and sell it in a few years.

I know new boats seem to hold thier value fairly well. So I probably wouldn't be loosing too much money if I sold a new boat two or three years down the road.

Any thought's or suggestions, would help me out. You all know way more about this than I do.
thanks