I did this last year in Vail, Colorado.
Vail is an exceptionally poor choice in terms of cheap living. I did, however, write a blog post which discusses some of the general aspects of a ski town as a digital nomad. As it turns out, new users can’t include links, but if you are interested in a detailed rundown, it’s currently the top post on my blog at thisisyouth (dot) org.
Some general notes:
Overall, ski towns are EXPENSIVE. Short-term accommodation is at a premium and the cost of living is higher than normal. Not a great bet for a cash-strapped nomad, although one who generates a more than few thousand in revenue a month would get by better. Turnover is high and a ton of seasonal employees come in and out of these places, so finding a room usually isn’t too hard, IF you’re willing to pay.
Lift tickets are also usually very expensive if you don’t buy a season pass, and season pass sales are usually halted sometime in November or December. So, not great for the spontaneous movement style of many nomads.
The skiing is great, and if you have a flexible schedule you have no reason to ever miss a powder day. However, you won’t find any entrepreneurial peers in the ski town, as almost everybody else is young, working in the service industry, and mostly there to ski and party.