I just bought my first boat a few months ago and can confirm a couple things that have been said - dont look for a FIRST boat, get every bit of boat you can afford. It will be a hell of a lot more expensive to have to sell your first boat for the boat you really want two years from now. I joined a local club and rode on a few boats, talked to a lot of folks and spent 6 months on craigslist and various other sites. I rode in 1 fish and ski learned enough to know not to get one. They are not very good to fish out of and not very good for taking people out in. I bass fish 90% of the time and the family can deal with not-optimal seating the other 10% of the time.
Be sure to add in everything you want/need on top of what you are paying for the boat. Taxes, graphs, new trolling motor, carpet, upholstery, repairs, etc. add up in a hurry.
I ended up with a 98 Bass Cat PII with a 200hp vmax. Its 19' (which fishes plenty big) and has a top end I havent found yet (somewhere over 65). It has a removable flipping deck so I can actually put 4-5 people in the boat if needed. I put on some used high end electronics that have enough features to keep me busy for a while too. Trolling motor is a 24 volt 80# (which I thought I couldnt want more - but already think about it on windy days).
That being said I learned a ton about bass boating since owning it and have discovered about 8 things that I should have prior to buying it. I could have negotiated more money off or at least gone with out that bad feeling when you discover a problem later. Look at a bunch even if you know you arent going to buy them. Just practicing talking to people about their boats will help. Take someone along that knows bass boats and/or pay the money and have a shop check out boat AND TRAILER thoroughly. Motor and transom are the big things but things like crappy wiring, rusting trailer, fuel issues, hydraulics, etc. can cost you $ks.