I thought I'd weigh in.
First, I think Vermont Act 250 is a good thing. The only problem with it was that people who really wanted to stop something could sue repeatedly to tie things up even though they had no particular ties to the town where the development was happening. I believe they have changed that aspect of the law recently. It didn't stop metro-Burlington from turning into New Jersey sprawl but it did manage to keep most of the rest of the state green.
Vermont Act 60 was the statewide school tax that caused the uproar in the resort towns. It was replaced by Act 68 which isn't any better. In my opinion, the big problem about Act 68 is that towns that opt to spend more than a statewide cap per-pupil get hit with a huge penalty. I forget the exact ratio but it's something like for every dollar they spend over the cap, they have to kick in $10 to a state pool. From where I sit, that's the politics of envy and very bad public policy. You want towns to vote to support gold plated schools with low student-teacher ratios and where they pay their staff reasonably to attract good talent. That aspect of the law is bad public policy. As a vacation home owner, I get taxed at the commercial rate and I complain about it but the commercial rate at Killington is actually lower than the residential rate because of the crazy penalties for exceeding the per-pupil cap that only apply to the residential school tax.
I like living in Portsmouth. I grew up on salt water and that's more important to me than having a ski resort in my back yard. Yep. Property prices are crazy. Rental prices aren't. I have a waterfront house (a very small one) on an acre of land with a boat dock. My rent is less than the property taxes would be if I bought the thing and reset the assessed value. KMart is 2 1/2 hours. Sunday River is 2 1/4 hours. Sugarloaf, Stowe, and Sugarbush/MRG are all 3-ish. You're not going to do them as a day trip very often but any would work fine for a weekender. I know lots of people who drive 4 or 5 hours each way every weekend.
If you held a gun at my head and said I had to move somewhere else in Northern New England and it couldn't just be to my place at Killington where I know tons of people, I'd consider Burlington, the upper valley, and Portland. Burlington has the lake and trivial access to some pretty good skiing. I went to UVM so I'm familiar with the place though it's gentrified incredibly since I was there. The upper valley at least lets you escape the Vermont and Maine tax structure but everything is still a haul. Portland gives you a great summer on Casco Bay, trivial day trip drive time to Sunday River, and a reasonable drive for weekends at Sugarloaf.
