Welcome to sailnet.
We (my wife is MMR here on sailnet) cruise out of the Magothy river, if you ever see us on our Gemini Catamaran (Patience Two
) feel free to swing by for a raft up and a Rum or two. We've sailed in much the same areas you have and spend most every other weekend somewhere on the eastern shore, mostly north of us at Fairlee, Still Pond or beyond.
There are a lot of options for slightly bigger boats that make good liveaboards, but I'd strongly recommend you go with one that has a diesel engine as the aux power over outboards. Diesel fuel is inherently safer, and you can generate power for your batteries.
The Annapolis area caters to sailors and there are lots of schools you can go to (including Anne Arundel Community College to save money) and take courses in diesel maintenance and repair, and other marine systems. I'd recommend buying pretty much anything Nigel Calder has published on boat system repair as the first step, reading through them to get an idea of the terms and such, then hanging out on the pier and talking to the old duffers who always hang out there. Most of the old salts are always glad to talk to a female, especially one with a little grease under her nails and a few rope burns on her hands.
If you ever want to crew on a friday night (come summer time of course) on a catamaran, give me or MMR a holler via PM - you'll have to have 10 posts to send a PM. We host the family friendly, low intensity cruiser style races for our Yacht Club *www.YCCSC.org*
fridays on the Magothy river.