I'd second Annapolis. Very sailing - oriented culture, forgiving sailing grounds (moderate winds, mud bottom no rocks to damage hull if you do go aground), lots of sailing schools/clubs, lots of boats for sail, lots of races to participate in if that interests you. No sailing for 3 months of winter but lots of free sailing-related seminars to keep your aquatic mind active. The downside is that the cost of living is higher than other areas; ya gets what ya pays for.
And, when you're ready to move aboard and start cruising you have lots of places to gunkhole, then easy access to the ICW to head south to the Bahamas/Caribbean.
I like the idea of Annapolis as well, but it has been more than 20 years since I have been there, so my vision may be a bit dated. But good sailing, good culture, seems like a nice place to raise kids. As you say it is expense, but as I understand it they have good schools, and services. Someplace like Florida where the cost of living is low, but services are too. Schools and other basic services seem to really be lacking. They seem to be getting worse as well. For me we have picked the last few houses with one thing in mind, the schools. My kids are almost out and they are both looking at top universities, so I think the decisions were worth it. You get what you pay for for the most part. Likely the best job market as well.
I would say without hesitation: Oriental, NC.
Lots of very quiet waters to sail on, relatively cheap prices, small community atmosphere, great boater support, nice climate allowing you to sail year round while still experiencing 4 seasons, close to both North and South great sailing destinations.
This seems to me to be the furthest place south I think I could live in the US (well perhaps the keys) Good weather but still have seasons and not too hot in the summer. Not sure about the schools, and the politics seem to be on a really weird path. (not being political, just points to a cultural change) Nice thing with NC is you can go a bit west for real mountains, and you have the beaches of the outer-banks. Seems to be a really nice spot. Not sure about the job market here though. (assuming that you have to build the cruising kitty) I would be interested in hearing about the job market in Oriental.
Don't they have very strict anti liveaboard rules? Beautiful city though.
Can you tell I have been thinking about moving? I love New York, but now that my kids are getting out of high school and starting college it is time for me to think of where I want to spend the rest of my working life. Perhaps I will follow them to Boston if they wind up at Harvard/MIT. (two of the top contending schools now)