Welcome Will,
I currently live in upstate New York (UNY). As I near RE I want to spend more time away from UNY, for 2 reasons only; snow and cold weather. I've endured it for 53 years and I'm ready for a change.
However if you enjoy the winters its a home run beacuse the other three seasons are among the very best anywhere. I like the mountainous areas in the eastern part of UNY. The Adirondacks and Catskills are hard to beat. I've spent a lot of time in Tompkins Co. Their motto is "TC is gorges". The rock formations and access to the finger lakes, not to mention Cornell U. makes it a cool place. St. Lawrence Co. could be THE place for you. Cost of living is relatively low, lots of wide open spaces. Same for parts of Sullivan Co., but watch out for "casino fever" there. Erie Co. read Buffalo (pronounced "buff-lo") is something else. The people I met there are positively convinced its the best place on the planet to live...must be something in the ice.
Here is a county-by-county link
http://www.nysegov.com/map-NY.cfm
Do your state tax and healthcare homework. These could be your biggest problems. But they likey will be only speed bumps not brick walls.
BUM