Some of the best ocean sailors have perished in very capable boats and Tinkerbelle, a 13 foot wooden makeshift boat, crossed the Atlantic with a skipper that had never been on the ocean before.
Luck has a bigger role in offshore sailing than many of us want to admit.
That said, one must assess the boat's and crew's ability to deal with bad luck to make this decision. For me, I want a boat that I can crawl below, strap in and ride out bad luck, or I want to be absolutely sure there is none on the horizon.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.