Hey waveshredder,
I have been shopping for my first boat lately too - and I have seen MANY boats in your price range, many of which are the types people have sailed to the Bahamas in.
also, you do not have to look just at the $10 and below range. Keep in mind most brokers list boats for more than they know it will sell for, usually 25% more, just so they have bargaining room.
Even If you see a boat for sale for 11K, even 12K, you can put an offer in for $9K, then do a survey, and if it's an older boat, and the surveyor finds flaws, you can always bargain lower
Just don't do what I did (Get all excited on an over-priced boat, then find out it's worth much less, better to put a lower offer on the boat first, and if it gets rejected, move up or move on)
It's kind of like adding salt to a meal. You can always add more salt if it doesn't taste right, hard to remove the salt if you've over salted your food :P