my situation: I am in my mid 30's and basically grew up on the bay. parents had cabin cruisers while I was young and I talked my dad into a 1971 - 31' Westerly sailboat when I got out of college. We had that boat 10+ years (and surprisinly it was really realiable) and he sold it 2 years ago. I also spent some time on club race sailboats from 19' - 45'.
Looking at late 80's to early 90's sail boats in the 30' range. Not looking for performance or bluewater capabilities. Just a day/weekend sailor for the Chesapeake. I want something a little newer and better amenities / more comfortable than the Westerly. basically Pearsons, Catalina's,Hunters, O'day, etc......