Looking to buy a boat in the DC area and have some questions
The first thing I would do if I were you is buy or borrow Don Casey''s "This Old Boat" and read the first chapter entitled "The Choice". You may not agree with his priority list of criteria for a suitable boat (he ranks appearance or beauty number one), but you need to consider all the good advice he offers, especially about cost and being realistic about how you will use the boat. Come up with your own ranking for which criteria are most important to you, and you''ll have a good basis to start looking.
Think about how handy you are and, more importantly, how much time you have to do maintenance and restoration. Don''t start by saying "I can afford a boat that costs 8 thousand" and latch onto a vintage 27 footer because it''s a "bargain". If you are a beginner sailer, I''d seriously consider starting with a Dinghy like a Lightning which can be easily trailered. Boats like these resell fairly well so you don''t necessarily have to get something you can "grow into" if you decide you want a cruiser for overnighting; and it will help you develop good sailing skills.
If you''re determined to get a cabin on your trailer sailer, I''d tend toward the smaller/recent vintage end of the size range, and try to find a "turnkey" boat at the upper end of your proposed budget. Smaller boats are cheaper to maintain, easier to set up and launch and retrieve, easier to park in your driveway/backyard, and if you get one in good shape you won''t need to do a lot of work on it before you''re ready to enjoy it. Buying a bigger, older boat will mean more restoration, higher maintenance costs, less time on the water, more time spent fixing and maintaining.
For the Potomac, a swing keel/centerboard cannot be beat. Outboard auxiliary and tiller steering by all means.