Yes, owners associations and websites devoted to the boat can be a great resource, but many boats don't have the luxury of having a strong owners association or website devoted to them.
I'd also agree that the seller is a huge variable. The reason they're selling is often key to getting to the truth of what the boat is really like and why it is priced the way it is. I'd disagree that people don't sell boats that they love because there are many reasons for selling a boat, many of which have little to do with the qualities or condition of the boat itself. I've seen boats that were being sold because the spouse wanted it gone... or they were getting divorced, or they were getting married, or they were moving, or they were getting too old to handle it... etc... none of which means has any reflection on whether it was or is a problem boat.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.