I lived in Burlington but it was 10 years ago. I would LOVE to go back and live in VT. My BFF went to Dartmouth at the time I lives in VT so I spent a lot of time there too. Burlington I the littlest biggest city- meaning its the smallest out of all of the biggest cities in each state. Burton snowboards is based there. COL is pretty high. And diversity is pretty low. It is a lot of rich, educated, liberal people. Lots of local produce, free trade, organic, farms type thing.
Living in Burlington I did not have a car and did just fine. I walked and rode my bike everywhere. I lived in Stowe for a month waiting for my apt to be ready and did fine with no car there too. I believe the big grocery store chain was Safeway. I know nothing about coupon/stockpiling so you're on your own there. I know I did a lot of shopping at a co-op too.
There is tons of outdoor family stuff to do, always. VT is gorgeous. I know it used to be, and I hope still is, that no billboards were allowed on the interstates which was nice.
I hope that helps some. I think jobs may be a little harder to come by- but most places are like that now. If I had the opportunity I would move back to VT.