Now those are some good questions.
I would start by calling the Virginia DMV to see whether he can keep a Virginia driver's license or whether he would need to change his driver's license to either New York or his home of record, Ohio. (The reason I would call VA and not NY would be that VA doesn't have a stake in this either way, whereas NY may give you the, "Oh, you need to change everything to NY spiel." as they tried with us.)
In general, how it works for non-military people, is this - when you move to a new state, for work, school, or any other reason, you have 30 days to change your driver's license and also to apply for new plates for your vehicle. In most states, changing your driver's license coming from another state is as easy as turning your current one in and getting a new one.
In the military, you can keep a driver's license from your home of record. Now, my husband got his first license in California where he also finished high school and joined the military, but his home of record is Virginia. He has a VA license and our Jeep is registered in Virginia.
As of January 2010, spouses can also keep their driver's license and vehicle registration in another state, whereas previously they had to change once they moved to another state (just like any other civilian who moves to another state). I believe that you can declare your home of record - so if your hubby's is VA, as a military spouse, you could make VA your home of record. (Don't hold me to that, though - we moved here before that went into effect and I had to get a NY license. I will eventually change it to hubby's home of record (VA), just haven't yet.)
I don't know how it works if you come in from overseas. That may be a question for the DMV and/or JAG?
You won't need to be up here.

I've never parallel parked in my life, except on the NY driving test.