YOu're not going to get a 38-42' boat for $20,000. Not one that is in decent shape anyways. Given your budget, you're probably better off looking at the 30-35' range, and closer to 30' realistically. I'd recommend you look at
James Baldwin's Boat List to get an idea of some good boats to look at.
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Sailingdog
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Telstar 28
New England
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.