Where would you actually live in this area? Serious question.
Depends on priorities. If cost is the ultimate consideration, live in San Luis Valley- South Fork, Monte Vista, Alamosa are dirt cheap, Alamosa has some blue/white collar jobs potential. This would make Wolf Creek your home area, put you in day ski range of Crested Butte, Taos, and Monarch. So, you know, heaven.
Or go to the other side of Wolf Creek pass and you have Pagosa, Bayfield, Durango. You can home mountain Wolf from Durango but it is about 1 1/2 hours. Purgatory/Hesperus is the local Durango mountains, and you are in day ski range to Telluride and Silverton. Live in Durango proper and your kid can ski afternoons at Chapman Hill downtown.
I live in the Foothills North of Bayfield. It takes a little over an hour to get to Purgatory and about 15 minutes longer to Wolf Creek. The extra travel time is well worth it for our home, which was quite affordable by Colorado standards, is on acreage, has National Forest access with great snowmobile terrain, and has a million dollar view.
Durango has the best job prospects down here. Both me and my wife work out of Durango though I am mostly work from home.
Why is it my favorite region? Well, it is the one both me and my wife managed to live and work in, but more objectively it has a bunch of never crowded mountains with top tier terrain, and then it has Wolf Creek, which along with Targhee and Powder Mountain has some of the best ratios of skier visits to snowfall in the west- and better terrain than it gets credit for. The new lifts help the perception of that terrain and the ski experience because they eliminate a lot of the long traverses on the runout and let you just ski downhill.