WHITEFISH! For sure. Awesome riding areas, and a ton of them within probably 2 hours, probably some of the best snow in the country. Cool town too.
We made a trip up there around Christmas this year, stayed in whitefish and rode 3 different areas over a 4 day period, and it may have become one of my favorite areas to ride (have ridden all over Wyoming, Montana and Colorado). We rode Lost Johnny (15 min from town), Red Meadow Lake/Olney (20 min from town), and Seeley Lake (2 hours). All are awesome areas, and I know there's a ton more places to ride from in that area. Like I said it is a cool town, really nice, and its right there at the base of the mountains, feels like a mountain town. And there are lots of towns nearby, Columbia Falls is right there and Kalispell is a good size town and only about 20 minutes away. Greybull is more isolated isn't as nice of a town (from what I remember, drove through real late earlier this year), and the riding is definitely not as good, It would probably be about an hour drive to where you ride in the Bighorns, you could go 2-3 hours and be in Togwotee, which is definitely a better area than the bighorns. For me it would be an easy choice- Whitefish. That being said I don't know which place is offering a better job, nor do I know what it costs to live in either place.