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Severan, by all means look for a racing team that's willing to let you sit on the rail for a couple of seasons while you learn the ropes. Or go to the public library and read everything you can about sailing, then go find a boat that's cheap enough to be considered "free", buy it, take it out on the water, and start praying.

If sailing is a skill you would consider valuable, you should be willing to pay a little bit to learn how to do it a little bit. Three days of lessons will go a long long way to kick-starting your sailing career, will make you more attractive to skippers looking for crew, and will probably cost less than a month's rent.

I would also reconsider your analyst job offers. Sailing lessons and a used 27' boat start to resemble "free stuff" when you start raking in a sizable salary (if you're a wise spender). Insist on a mariner's career and sailing will probably always be very expensive to you.
 
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