My first boat was an old canoe that i found at my grandparents house. It came equipped with a human powered paddle trolling motor. LOL! After about 6 months of that I saved my money and bought a 1976 terry bass boat for $2000, which i found in the newspaper (best time to look is in the winter, thats when you will find the best deals). And unfortunately it now has a tree limb through the hull and it would cost more than i paid for the boat to fix it. :'( So I am currently looking for another boat.
I found that the best thing to do is look everyday and go and look at several boats in your price range to get a general idea of what is in your price range, because words and pics only say so much.