Man there's a lot of different factors to consider. I am more of a southern New England resident but enjoy traveling to northern New England, particularly to Maine where our family has a cabin. I'm quite happy with the area I live in now as I am close to family and geographically I can get to the CT shore and Southern VT in an hour. Close to Springfield and Hartford and not an unreasonable drive to Worcester, Boston or New York. I have an abundance of shopping and restaurants within 5-10 minutes of my house , only a couple miles from interstate 91 in a suburban setting but can easily travel to more rural areas in 20 minutes. If I had to make a trade, I would give up some of the convenience for some additional snowfall with elevation, more hilly terrain, and classic colonial architecture Perhaps somewhere on the east slopes of the Berkshires or Litchfield Hills, but not really far out there, like a Barkhamsted CT or a Granville Mass at 1k+ where you could still drive down to the valley in 15-20 minutes where there is shopping and conveniences.