Grew up in Western MA, college at UVM, moved to Florida in 1980, in 2002 bought house in S. Vermont, spent about 8 months a year there for 13 years and 4 months a year in Maine since.

Getting out of Florida will do wonders for your outlook, unbelievable what is happening now. Hilltowns outside Northampton are great, due to 5 college area. Housing grows more expensive closer you get to Northampton. Greenfield is sort of funky but nice. I know Brattleboro in S Vermont well and the area is very liberal, a bit on the feeling superior side. But very nice people and a place you could enjoy, I believe (as you could Western MA). Brattleboro housing is much more affordable. Tax wise what you save in insurance will disappear in property taxes plus you have sales tax and income tax (Vermont & MA). Both states have outrageous taxes, compared to Florida. New Hampshire wins tax-wise. One thing you may think about, unlike Florida where school systems are county wide, in New England each town has a school board that sets school budgets and really determines the quality of education. Research well, great variances. Good Luck.