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Re: Sailing alone??
One funny thing I have learned is that many bigger boats are easier to sail single-handed than smaller boats. Bigger and heavier boats (e.g. my Gulfstar 41) tend to react much more slowly and gracefully than twitchy little light boats, giving more time for the single-hander to get everything done for the maneuver.
OTOH, one should learn to sail on the smaller, lighter 'twitchy' boat for exactly that reason -- good, quick feedback :-)