Re: Very n00b questions from a prospective sailor.
I registered an account to reply to your message. I'd recommend that before you buy a boat, you join a sailing club. There are a bunch on the Hudson in both NJ and NY. A bit over a year ago, I joined one (HRCS) with no sailing experience at all. I had read one of those "intro to sailing boats," so I sorta knew what the parts of the boat were. I didn't take any classes, but I went out on an instructor-led sail or two, before going on sails with other members. I soon got in with a bad crowd (racers) and during the last fall and spring and summer of this year, I've been out about 3 days every week. I never did get around to taking a class.
The membership fees are quite reasonable, especially compared with paying for a mooring spot. The nice part about the New York area is that there are enough people that sailing clubs work really well. I personally know of Hudson River Community Sailing, the Manhattan Sailing Club, the Hoboken Sailing Club, and SailNY. There are probably more.