I'd avoid wooden boats. From what I've seen of most wooden boats, the maintenance is far higher, and you'll be spend far more time maintaining the boat than you would on a fiberglass boat. Most people who have never owned a wooden boat have no real idea of the massive amount of maintenance they require, especially compared to a boat made of "frozen snot" as one old timer referred to fiberglass.
One boat that may fit your requirements, as a liveaboard, coastal cruiser, but is fairly capable as a bluewater boat is an Alberg 30 or Pearson Triton. Both of these are Alberg-designed boats, and quite capable boats, with fairly good light air performance as well. They are both reasonably priced and simple to single hand as well.
Of course neither of these boats was built as a "blue water passagemaker" as both were designed before people had such silly classifications for boats.
If you're curious about the capabilities of the Triton, try looking at this website
. The Alberg 30 is basically a larger, refined version of the Triton IIRC.
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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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