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Old 12-14-2010
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First, it'd really help if you had a rough budget in mind... that will eliminate/reduce what choices you have. I also recommend keeping 15-20% of the total purchasing budget aside for refitting, upgrading and modifying whatever boat you do buy.

I'd also ask how much actual sailing experience do you and your spouse actually have? Do you know whether you'll get seasick on a boat in a rolly harbor? You say you have a couple of trips on a keelboat, but that could mean a couple of daysails, so how much real time have you spent aboard?

Also, why are you limiting it to monohulls? There are a good number of small cruising catamarans that would probably be a good fit, if not a better fit than many of the monohulls you've listed. The Prout Snowgoose, the Gemini 105 Mc, etc. would give you at least as much interior living space and be far more comfortable at anchor than the monohulls.

I'd recommend you read the Boat Inspection Trip Tips thread I started, as it will help you determine whether any boats you look at are even worth going forward on, saving you the price of a survey on boats that aren't worth looking at further.
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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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