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Haunt Ebay for cheap boats. An Ike damaged V40 just sold for less than $25,000 as an example. The boat had cosmetic damage and a broken mast. Mast could possibly have been repaired cheap with a sleeve. The rest was just paint and elbow grease. All the systems were reported to be inspected and working. Have seen a Bristol 32 go for less than $13,000 in good condition and some boats under $10,000 that needed cosmetic work.
Cheap boats are out there, you just have to make stupid offers.
Do be aware that cruising gear is expensive to add. A windvane is $3,500 plus, a good auto-pilot $2,000 plus and closer to $5,000 when you figure in the spares and gear to feed it's electron hungry appetite, a new dinghy and motor are upwards of $2,000, self tailing winches more than $2,000, new sails close to 10 big ones, etc. Buying used can cut the cost way down but doubt that you could untie the dock lines for under $5,000 on a boat that hasn't any gear.
Having said the above, other than the self steering vane, most of the stuff is really things that you can get by without. Bedroom sheets will get you a long ways though not the fastest.
Aloha
Peter O.
Pearson 35 #109
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