Bennington sucks, and I believe there's a no shooting law within city limits. It's one of the few exceptions to the state-wide Sportsman's law that prevents towns from enacting any sort of local gun control. That said, any neighboring town is going to offer a rural setting where you can more or less do whatever you want. If you have kids, finding a nearby town with a good school may be a challenge. Most of the nearby towns have very small populations, and likewise, very small schools. My kid goes to a school that has 40 kids TOTAL in k-8. Generally the towns with higher taxes are the more wealthy towns, which also have better schools.
Property taxes are high, but compared to NY, they're great.
Bennington doesn't get a whole lot of snow, but if you go 10 minutes west into Woodford, it might as well be Alaska.
Yes, you can run studded tires. MA requires them to be off the car by May 1, but I'm not sure if VT has a similar requirement.
Yes, VT requires vehicle inspections, but there are plenty of small garages that will put a sticker on anything. No smog checks.
The roads are a mixed bag during bad weather. Generally the state-maintained roads are awful because the state seems to have an aversion to salting the roads until a week after it stops snowing. Most of the towns do a decent job with their local roads.