I think the Tartan 30 would be a much better sailing boat than the Vanguard. It would certainly be a better performer in the light air that you often see in Long Island Sound.
Another good choice would be something like an O'Day 302 or 322.
Given where you're located, I'd avoid the full-keel designs, as they're going to have a significant performance penalty.
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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.