I have to agree with ryoungbronco - he's right about Jersey. The reason you are moving (for your son) is what you should worry about. There are some really great schools in Jersey and specialists in NYC that will be able to help you out.
As for your lift question - are you asking because of the local laws, or because you want to know if you need something else for the terrain? The laws can be gotten around for the most part (we are known in Jersey for our corruption!) and I've seen pickups on the road that I can stand under and not hit my head on the tranny. As for the terrain, well, South Jersey has a lot of sand trails and beaches, you could go to PA or southern NY state which are the start of the foothills of the Catskills. There is a lot of slate in the area, and some larger type boulders and whatnot.
Mud pits are around, but you need to look for them, and depending on where you are, the snow can be great to wheel in, or so minimal that you won't even need to think about owning a snow shovel.
As for anything else - I can't speak for VA, but I know that in Jersey, you'll pay more in taxes, but everything is included. Northeastern Jersey sucks for traffic because a lot of commuters live there who work in NYC. Northwestern Jersey has better areas for offroading and is more open and mountainous, but the schools aren't quite as good and the winters can get a little rough. PA is more like northwestern Jersey, but the taxes are different - you wind up paying for everything out of pocket. Your property taxes are lower, but you need to pay extra for schools and garbage pickup and other stuff. (Don't ask me why).
Basically, you can be anywhere you want in 45 minutes or so. NYC, skiing in PA, the Jersey Shore - whatever suits your fancy.
I think I got off topic. If you are worried about the lift laws, there may be something on the NJ MVC website.
