VincentVega's offer is a pretty good one!
But, if you do decide to get your own "trainer" sailboat, I'd suggest you take a look at the Beneteau First 235 with a wing keel.* Easy to trailer and the cabin is very efficient, including a chart table and marine head. With the wing keel, you'll be able to go more places where the water's too shallow for some of the other boats. The fractional rig will be easier to single-handle in a breeze. And, it's a boat that you'll have no trouble reselling when it's time to get your big boat. Check it out...
Beneteau First 235 - A pocket racer with cruising aspirations! beneteau235.com
Beneteau First 235 Forums :: Index
*
Disclosure - I don't own a Bene 235, but would definitely buy one if I was going to stick around the DC metro area longer-term and sail/cruise on the Chesapeake.