Hi all, just catching up to this thread now. I've been in Vermont for just over 2 years (landed a new job here- in hindsight, so lucky on the timing of that!). We moved from MA and I grew up in the NY/NJ area. I live in South Burlington, since moving I've skied Bolton Valley, Smuggler's, Sugarbush, and Stowe (plus Cochran's!). We love the SB school system and it's close to work (yep, I still have to show up in person) though a bit of a drive to the mountains. I don't know the other towns so well, but I know a few people from Richmond who really seem to love their town and schools, and it gets you a bit closer to the mountains (plus Cochran's is pretty much in your backyard).
Bolton is the closest to me, I think my overall favorite has been Sugarbush, and I've skied Smuggs the most and know it the best now. They have a great locals lessons program for kids and run a women's program at the same time (I've posted my love for it a few times on this board I think). The two women in my ski class last year were both from Cambridge (where Smuggs is), both had kids, and both seem pretty happy with the school system. Their kids both started at the Smuggs lessons programs when younger but they moved on to the racing program run by the Ski & Snowboard Club, which seems to have a pretty great program.
My in-laws have had a condo in Manchester VT for a number of years so I know that area somewhat. It is a great little town to visit, though I can't speak to the school system. I've skied both Bromley and Stratton-- Bromley is more laid back but smaller, Stratton has a lot more terrain.
I just remembered that a Boston area friend was able to rent a house in Stowe at the start of the pandemic. When school started in-person this fall (most VT schools are either fully in-person or have a hybrid program), she was really happy- her son really blossomed after struggling the the Cambridge MA school system.
Re some of the other thoughts on this thread-- I grew up in the greater NYC area, my husband is from upstate NY, and we lived upstate for a few years... there is DEFINITELY a big difference (and some animus) between upstaters and city folk! When I lived in MA, I guess I was lucky to live in a snow/ski loving neighborhood when we were there...great memories of all our kids out building snowmen and having snowball fights after the big storms. We used to meet up with our neighbors to ski at Wachusett. Also, I'm so glad I found my job and house before the big influx of new Vermonters, but I've been daydreaming about either renovating our house or buying a mountain house, looks like both of those may be on the back burner for a while.
I have heard 2 things about the influx of new Vermonters. Yes it's driving up housing costs. But, VT has had a declining population for a while which is not good for the tax base-- the state has actually been trying to attract remote workers to move here for a while (there was a monetary incentive I think). I'm no economist so I don't know what's best in the long run... the housing crunch needs to be figured out, and hopefully VT doesn't get too built up either or it will lose the thing that makes it great.
Good luck in your search! And, SkiVT2, I feel for you!