The O'Day 28. It's a step above trailer sailing with the ability to do short trips, and not a prohibitive entry cost, in case the admiral doesn't want to pursue the sailing life.
I thought that might be the boat you were thinking of. The O'Day 28 is the boat I rented there, and more importantly, my family owned one for 5 years when I was a teenager. Also have a friend who had one a few years ago. I'm pretty familiar with O'Day 28s, although I haven't owned one as an adult, so I'm sure there are others out there who are far better experts on maintenance issues, etc.
I don't think you can beat the amount of room for the size and price range of these boats. Our family of 4 sailed ours all over the Bay for weeks at a time, and even sailed round trip from VA to Newport, RI and back. I've seen a number of them in poor condition, and only an occasional decent one. But if you can find a decent one for a good price, I think it can be a good boat for the money.
Good luck in your "research"!
-J