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I read this whole thread... And having bought a boat with similar goals less than six months ago, I want to throw my 2 cents in here.
The OP seems to be on the fence about what exactly he wants.. but assuming you're after something 25-30' you can get a decent boat for MUCH less than 20k.
Maybe I'm not in tune with the rest of the country, but the economy right now has put a new meaning of "buyer's market"
My only worry is that I might find 25' too small. Plenty enough room for our family of three, but the pop-top seems like it wouldn't be great for added guests, as I figure nobody should sit on top of it. I also worry about it handling rougher seas like some ~3ft ones I saw this summer coming home across the Sound in the evening. I figure I could maybe get it for $10k (13.5k asking price) by leveraging some comps. I'd have that "pride of ownership" and ability to sail at will. I think I might always be "what-if"ing myself regarding a larger boat, though, and it'd be nice to have more main-cabin berthing without building a custom insert."
Anyone selling anything right now in your price range falls into three categories:
A. boat has been on the market for far too long, obviously overpriced
B. Boat just got on the market from a non-distressed seller, who probably wont be able to get what he wants for it because of market conditions
C. boat is on the market from a distressed seller who needs to move this item.
You have a kid on the way, what you want is flexible (many types and makes will suit you) and you are trying to save money. I'd find some people in the "C" category, and offer, at absolute maximum, 60% of the asking price, unless the boat is listed at an already very low price.
I got a 1983 27' tanzer for significantly less than 10k. Price had dropped twice and I told the broker straight up that I had cash in hand, and if the owner wanted to sell that I needed an answer quickly or I'd just move on. They didnt even counter my offer. It needed a few routine things, but other than bottom paint, she was ready to sail that day. Six months later I've had no major problems, and I still have less than 10k into her, counting survey, all repairs, and painting I've done. My only regret, having seen the economy deteriorate even more since the summer, was offering what I did.
Shop around. Do tons of research. Get a surveyor. Do NOT pay too much money. Its a buyers market, and its only going to get worse for the sellers in the near future. Now is a great time to be buying a boat, if you can reasonably rely on your future income and job situation.
Last edited by southernsmoke; 01-28-2009 at 05:14 PM.