The sailing bug recently bit me hard. Just completed ASA 101, 103, & 104 in the BVI. Looking for all the experience and advice I can get on sailing, and living aboard with the notion of cruising in the not too distant future. I've begun a slow and deliberate exploration of all things sailing, using this, other forums, and extensive reading (e.g. Vigor, Kretschmer, Calder, and Casey, etc.).
Welcome to Cruisers Forum. I used to live about 50 minutes north of you, on a little creek off the Bay. Great sailing and gunk-holing in that area.
You're off to a good start with the sailing courses and reading lists. I'd recommend doing some chartering on different kinds of boats as a good way to solidify the skills you've developed in the sailing courses, and also to help you decide what you like and don't like about boat features.
I almost got stationed at Yorktown for my last tour in the Navy. Went to Pearl Harbor instead. I like your area and it offers a lot of sailing opportunities. My niece was instructing at VIMS there until a year ago.
No, I do not live aboard. The boss informed me that we were not going to sell the homestead and go sailing, so I have had to readjust my thinking. To save money, I am currently thinking about having the utilities turned off for the period of time that we would be sailing. I have to do more research on the cost of turning on and off the utilities. In June 09 I plan to retire and spend fulltime working on Scallywag, so she is in cruising condition.