I have a 1988 O''Day 322 and I really enjoy here. I also cruise the New England area. I''ve spent one weekend with a very active 5 year old on board along with two teenagers and two adults. While a little cramped with all of us there was enough room. I enjoy the winged keel sailing - although some will tell if you get in stuck in sand it''s just liked a Danforth.... I haven''t managed to do that yet at least! Maintenance is easy and access is good for the most part. The O''Day list here is very active and a great group!
I''d sign up and get their opinions too.