Generally, prices on boats go down as you go south. One reason for this is that a twenty year old boat in New England or the Great Lakes may see only half the wear, tear and abuse of a boat further south, since most are hauled out for the winter. The more intense UV also does a number on the gelcoat, paint, sails and other materials used on a boat. Twenty year old sails in New England may still be usable, not great but usable... ten year old sails in Florida are usually shot due to the greater UV exposure.
If your total budget is $50,000, I would recommend you look at boats priced from $35,000-45,000 and leave yourself at least $10,000 for re-fitting, modifying, upgrading and repairing whatever boat you get.
Just remember, in most cases, the asking price and the real selling price aren't exactly the same thing, with a 15-20% difference between the two in most cases...
BTW, lots of good boats in that price range. I'd highly recommend you look at James Baldwin's Boat List as well, at least if you're interested in eventually going further away than a week long cruise. LINK
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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.