I have lived in Annapolis, MD my whole life, (well except for going to college in VA). But anyways, the town and state are great. My only question is what part of the state you were thinking.
I live in Annapolis, which is the capital. It is a small city with a lot of suburbs. The city is great in that it has cute shops, a good bar atmosphere, and it's on the WATER!! It also has a high cost of living (which most of the state does, the eastern shore is a bit cheaper), but that doesn't mean that it's hard to live. Incomes are all across the board. Waterfront is WAY WAY EXPENSIVE now though! It is a good haven for small businesses and a lot of people prosper. We have four seasons and do get snow; however, people are pretty good drivers in it. It is only about an hour to both DC and Baltimore which provide lots of entertainment opportunities.
Annapolis is also part of the Beltway crew of MD. This means, that for a lot of people, they live somewhat near the beltway, commute to DC and have a high cost of living. Southern Maryland is more suburban, with a lot of people commuting to DC/Balt. Northern MD is more Baltimore oriented and I'm not that familiar being a kid whose parents work in DC. The eastern shore is great, very diverse, more rural. Ocean city is over there, which is a big destination in the summer. Again, not too familiar, we summer in Massachusetts. Northwestern MD, I have no idea, but you can go skiing in the winter.
If you're thinking MD, you may also want to check Northern/Eastern VA. It is similar to Eastern MD; however, near Fredericksburg and south cost of living is cheaper. I went to college in Newport News, VA between Williamsburg and Norfolk/Virginia Beach. The eastern part of VA down to the beach is really diverse, with a broad spectrum of people and stuff to do. (Nothing against western, just don't know about it).
Ok this post is long enough, hope this helps a bit. Definitely visit some places to get a feel for the area.
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