Where do you sail? I have been looking to get into it. My goal was to help out on current races and get into it that way. (I hear people need all the help they can get and will let you come along for free). I'm near Baltimore so there are a few active sailing clubs around here.
I sail at the Manhattan Sailing Club. http://myc.org membership is reasonable, about the same cost as a gym membership.
Racing is even cheaper if you know what you are doing. The words you are looking for is "rail meat". When the boat is going upwind it heels over, you need people on the uphill side of the boat on the rail. Being rail meat require very little knowledge. I would try to go out on days with unpleasant weather, fewer people show up. Rosh Hashanah was the first time I got out on Long Island sound (the boat had a very hard time finding crew that Saturday).
Try the Annapolis races, I'm not sure of where they meet, but you could probably get out on Wednesday nights and Saturdays.
