i live in mass. Of the 3 you listed Ive been to CO and UT. 99% sure ill be going to jackson this winter. All out of logan.
Im going to assume you have Summit County CO (breck,copper ETC) and Park City UT in mind, Along with Jackson Hole WY.
From a travel standpoint....
You cant fly to jackson non-stop like you can DIA (denver international airport) and SLC(salt lake city airport).
Between DIA and summit county CAN be a HORROR
show. Dont quote me but i think its like an hour and a half. Although coming from the east coast I-70 is epic your first couple of times. IDK of any cheap easy transportation from airport to slopes. I had the luxury of friends in the area, and also did the rental car thing another trip.
Going between SLC and Park City is wiked easy. like 45 minutes, 80 buck round trip shuttle, no worries. A bus to SLC itself was like 6 bucks 1 way if you wanted to check out the city n shit.
From what ive found so far jackson seems just as easy as SLC. Ive only looked quick here and there for flights, no trouble finding 1 stop each way round trips. Cheap shuttle from the airport to the slopes, just like salt lake.
Park City is loaded with bars
Ill leave what mountains best suite what your tryna do to some of the local cats on the forum.