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A couple of thoughts ...
So you've got $2000, but your car (if you can get a hitch for it) is safe and appropriate for lightweight boats. There's an opportunity (sounds like) to get a slip next year. So I'd have to side with the idea of hanging out at the harbor or club, catch rides on other people's boats, get a better sense of what you want to own, and go from there. Things being what they are in the economy, buying a larger vehicle in the hopes of finding a boat to tow and launch seems upside down. Buying a boat with limited sailing experience and then having to buy a vehicle seems like you're getting ahead of yourself.
Determine what you like to sail and then start shopping.
Good luck!
Kurt
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