Well conditions/terrain open really varies from resort to resort, keep an eye on them. If I had to choose one and the conditions were equal, I would choose Stowe. Its by far the nicest/most affluent resort, looks like a ski town, and has Burlington close by which is a stunning town. Jay is in the middle of nothing, Killington is big but a bit of a zoo and it isnt really a ski town, just an access road with a few bars/shops on it.

I have honestly never really done the tourist thing in Boston, I have been living here on and off for the last 4 years, and I love it. There is a lot of touristy things to do near government center, even one of those daft duck busses that goes in the sea for a bit then drives around town - they are open top though, and im not sure how warm it will be in 3 weeks - saying that today I worked in shorts and flip flops!

Jay Peak is FAR!!! It's a 8 or 9 hour drive from NYC.

Killington might be your best bet. It usually has the best early season snow and an OK nightlife. You can also get 2-1 early season tickets there:
http://www.killington.com/winter/2for1/2for1-dmbfan12/

So the Mrs. might not have an excuse not to join you on the Mountain.

If you would like to stay closer to NYC Hunter MTN might be open by late November. It's only 2 1/2 hrs from NYC but it is small and is really only good for a day trip. And expect very raw conditions there.