Here is what I would be asking myself if I were buying a boat:
1) What do I plan on doing with the boat?
-> Fishing, Skiiing, swimming, crusing overnight, etc? NOw put them order of priority. Fishing boats tend to make poor crusiers. Cruisers tend to make poor skiing and fishing boats.
2) Where do you plan on boating?
-> The boat pictured above is probably not the best boat for the ocean. A 34ft. flybridge is probably not great for a small freshwater lake.
3) Whom do I plan on boating with?
-> Is the list of things that I plan on doing with teh boat match the other people involved? Most wives don't want to fish. Most Kids wnat to ski, tube, and swim. Is everyone's interests being accounted for?
4) How much money am I willing to spend.
-> Not just for the boat, for storage, maintenance, fuel, repairs. I gurantee you however much you think you need to budget, it won't e enough. The monthly cost of a boat is higher than anyone anticipates. Those of us who love it enough, simply stop looking or caring.
A Boat is an excercise in compromise. When I started looking for my first boat I wanted a 22-24ft walkaround for fishing. I ended up with an express cruiser because that is the compromise I made to get my wife to join me every weekend. I've neverf regretted it.