I'd first highly recommend you look at James Baldwin's Boat list
. There are quite a few affordable bluewater capable boats on that list. I know of at least three that have sold within your budget range in the last year. One was a beautifully equipped Southern Cross 28, another was an Alberg 30 and the last was an Elizabethan. I'd also recommend you visit Sailfar.net's forums
, which is a forum that specializes in small boat cruising.
You plan to work from daysailing, coastal cruising up to bluewater sailing is a good one. Good luck.
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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.