I would check out some of the larger used Passports. Tayanas, Masons or even a Gozzard. These are primarily cruising boats.
If you are looking for a Bay boat with a performace side to it Sabre
or the Tartans are nice.
If you feel you want to go the mass production route
, Catalina has a better esale value than Hnter or Benne on the average.
The production boats offer more "condo " type accutrements as CNC40 has stated, but may not be the best for sailing and their tankage as well as rudder
protection may not be the best for offshore
As far as ease of handling...40-45 is optimal size for two people . Pick a boat that has a variety of sailing plans ( ie detachable stay) for the ability to adjust you sailing from the light air of the Chessie to the strong steadies of the tropics.
I keep my boat in Pasadena also on Rock Creek. where you are. Feel free to PM me and we can exchange phone
numbers. We keep our boat at the Maryland