I grew up in NYC and lived in Central NY for about 5 years. Flagstaff most reminds me of Oneanta, NY- a small railroad and college town in the mountains, except Flag has a lot more students.
I'd love to have a place in the pines, but have never been able to find employment to replace my income in Phoenix, even though the cost per sq/ft is every bit as expensive for a decent house in Flagstaff.
My suggestion is a place big enough for ADV gatherings and minimum a spare room to rent me in the summer months.
Flagstaff is a pretty liberal town (as most college towns are) compared to the rest of Arizona. I was amazed coming to AZ at the amount of usable open space to ride, camp, shoot and generally do what you want with little restrictions.
Good luck in your search and keep us posted!