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Thats a good point. In this market, you should under bid by a lot. You never know who wants to just get rid of it. If he says no and does not come back with a counter, you are way off base. In this market I would bid at least 25% under. "Blue book" value is useless right now. Anyway, its always about what people will take, not what the book says. If he says no, keep looking. You will have a year or two here to find some good deals on some good boats. From just talking to a broker friend, good boats under 50k are still going quick, especially Catalinas (people want the most popular name for easy resell). The best deals are the production boats over 100k that people thought they could afford but realized they can't, and the more limited, lessor known production boats that are fully outfitted and the owner is moving on.
As for what its going to cost you. Take the number you think, and add 50%. Seriously. Especially in the first year. The other thing to consider is that if you have a house, a boat will make it like you own two houses. Its a lot of continuous work to stay on top of.
Best of luck to you. Even though my response is a bit discouraging, I still love sailing.
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Great men always have too much sail up. - Christopher Buckley
Vaya con Dios
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