Re: who knows about sailing and sailboats?
I'd buy a dingy to start off with. The last thing you need is to run a 40k boat aground. I've sailed 420's and Flying Juniors at the college level. Both will be great learning platforms and lots of fun. To sail the bigger keelboats you also need competent crew members, but if you feel comfortable sailing and giving instructions you could take a 2man dingy out with a rank beginner without much problems. If you want to learn on your own a Laser is the way to go.
-SmileyEH
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