SoCal to Wisconsin by way of Alberta? WTF!?!?
OP: Congrats and thank you for your service!!! Colorado offers a HUGE variety of snow and terrain. (Wolf Creek, Silverton) tend to get much more snow (and fewer people) than the hills in Summit County (Breck, Vail, A-Basin.) For example, Wolf Creek has gotten 246 inches so far, Vail has 165, Telluride: 139. HUGE difference!
If you went through Pagossa Springs, you would be hitting Wolf Creek. If you are going the direct route, through Grand Junction, then Vail/Beaver Creek/Loveland would be your best bet. Snow is starting to ramp-up a bit, now. Finally.
Of course, there is always Salt Lake City, but that'll take you out of your way a bit.
Traveling the States and Taking Pictures