I agree that buying too big a boat is a good way to get into trouble. The suggestion for the Catalina 250 is a pretty good one, as you probably will sail more if you have to do less to get sailing. It will cost more to go that route, both as the boat is probably a bit more money, and the slip fees are a bit more than storing it on the trailer in your back yard.
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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.