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A good choice would be an Alberg 30. Carl Alberg didn't know how to design an ugly boat. One in decent shape would fall within your budget and probably leave you a bit leftover for modifications/refitting/upgrades.
They're pretty solid, definitely bluewater capable, and large enough for you to liveaboard.
Other good choices would be the Southern Cross 28/31, although you have to be careful since this was designed with an Airex cored hull, and water intrusion into the hull laminate is a potential problem.
The Westsail 32 is another possibility, but probably out of your price range. The Cape Dory line of boats are another good option, as are the Pearson Tritons and Ariels, but the Ariels are a bit tight on space.
You really should check out John Vigor's 20 Small Sailboats To Take you Anywhere... as many of these boats I've listed are there.
All of the boat's I've listed are basic sloop-rigged boats... single mast, head sail, main sail... fairly simple to rig, fairly simple to sail.
I hope this helps.
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Sailingdog
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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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