I actually live in Billings
So I actually live in Billings... and probably are on the same way length as you...
So Billings as a city: Not where I'm gonna be long term. Lack of a sense community, lame night life, lot's of blue collar folks who have never even been to the beartooth mountains. Do not get me wrong there are some beautiful spots in Billings along the Rims. While there are some good folks around, the per capita the type of progressive or outdoor minded folk I prefer to hang with... the concentration is pretty small and disappointing. Art scene... negligible. Music... hope you like hick cover bands that can't fathom original music. The town just doesn't feel young, fresh, or alive most of the time.
Boating: I'm creeking mostly and I actually would argue access to class V is pretty good in Billings and often overlooked by Bozeman folk. this past season I got 7-9 laps down the woodbine section of the Stillwater and mostly after work (here's some video of after work stillwater this year:
The Stillwater River on Vimeo). There's the west stillwater as well as the pots sections. The rock creek and rosebud drainages are right there too... more laps than I can count on those 5 separate runs. Then we get over to the Clarks Fork area as well... honeymoon, day stretch, lower clark's, crandall creek, sunlight creek.. and of course: the box. You go a little farther you get... the Boulder River, Big Timber. Most of this is within an 1.5 hrs of Billings and it's only 2 hrs of to Boz town. The paddling community is small... there only a couple of us "locals" trying to get after it and admittedly I'm in/near red lodge 90% of the paddling season. All in all, I count more than 10 IV-V creeking opportunities within an hour of here!
If you are looking for playboating... thin pickings. I have yet to find something worth getting on somewhat nearby. High quality stuff is only around for a short time and hard to access. It's pretty frustrating in a playboating sense.
Mtn Biking: Good shit right in town.... lots of sandstone slick rock. Plenty of stuff for me to take some good diggers on. Decent bike community around here for sure. The entire Rim for miles has Mtn Bkiing trails snaking all over it.
Skiing: If you are looking for resort skiing... stay out of Billings. While red lodge is a great little resort with a small town feel and support. Those who want the big resort feel and amenities should go to Bozeman. But then again you do your fair share of yuppie dodging over there. That being said, that's not what I want. However, the backcountry access from Billings is good. I'll be on my snowmobile getting after laps in cooke city most weekends and come spring... Bozeman folk flock to the Beartooth pass in Red Lodge... was skiing laps till 4th of July up there two seasons ago. So if you want backcountry skiing... it's amazing, but requires a sled.
Ice and Rock Climbing: Some of the best ice in the world is in Cody, WY... only 2 hrs from here. Lot's of ice climbers in Billings who get out and get after it. Tight little community. Rock climbing is in town and real good bouldering... but poor quality sandstone. Lot's of folks make the drive to Tensleep for sport climbing abound!!! There is alpine trad and first ascent to be had in the beartooths for sure!
Thankfully, you have a wife...which makes Billings even more tolerable. the women out here: they leave a lot left to be desired...
So as one of the few Buzzards living in Billings currently... that my two cents in the matter. Happy to answer more questions...