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anxiety in buying a boat
Seems to me a missed point here is that it took three people to put a reef in the main when the wind piped up. Any 36 footer which requires three people to reef the main would be out of the question, in my mind. Especially for a first boat on which one of the crew is not a sailor.
I would look for a different Catalina 36 if everything else about this boat seems right.
In mast reefing was never a good idea, in my opinion.
Best of luck.
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