I think the SO35 would make a decent coastal cruiser and liveaboard for the next few years. Get the older boat, and learn proper sail trim... and how to reef a mainsail using slab reefing... Slab reefing generally gives you far better sail shape than any in-mast reefing system ever will. The baggier shape of the in-mast reefed sail makes it more dangerous IMHO, since it is going to be powered up when you're trying to de-power the boat.
Look forward to hearing how it works out for you.
Thanks for clarifying for me...
I can be a little blunter than I probably should be...
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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.