I used to frostbite up in Marblehead, in Interclubs. Best way to get lots of good dinghy/racing (and therefore good sailing) experience. And in the inexpensive dinghies, it's more "democratic", no one can really outspend you on gear/sails etc the way they can in the summer racing.
Win a frostbite race, and chances are you've just beaten some America's cup guys, some national champions or olympians. Heady stuff. You'll also learn the racing rules backwards and forwards.
Experience like this is priceless--and cheap too. Well worth being a little cold sometimes.