Re: Champagne taste on a beer budget
Let me offer another perspective. If I had the $$ for a boat and was a DC Apartment dweller, I would want a boat comfortable for weekending so I could get out of the city in the summer.
I was going to suggest a Sabre 28, might be a good choice, but something like a Catalina 30, that's roomy, a decent light air boat and plentiful might be a better choice for your first Chesapeake Bay boat.
Personally, I think there are lots of days when anything less than about 30' really suffers on the bay. Those small boats just don't look like much fun on those days with 20 knots and a good chop going.
s/v Palmetto Moon
1991 Catalina 36