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Old 03-25-2010
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Well, I'd suggest spending the first $500 on some good books on seaworthiness ("Seaworthiness the Forgotten Factor; Fasnet Force10) and disasters caused by the lack of it, along with similar topics so you can see what the pros have to suggest in terms of boats that either won't flip, or will recover politely from flipping.

Along with spending some time looking at older threads, here and elsewhere, with titles like "Good first cruising boat??" where folks have asked these many questions and spent many hours discussing them.

1/4mil is plenty of budget, but unless it is pocket change for you, it is research that will be the most valuable investment you can make.
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