Good advice there. Wherever you go, you won't have a chance of finding a place to live unless you go very early. Used to be October-November was the latest you could go - could be September now (but no jobs yet, so have some money saved up or just pay rent and keep your old job until the season starts).
Vail is the best mountain for the type of skiing I like to do, but all of CO has good skiing. Pick the place that seems like "you." (FWIW, I understand there's a traffic jam going into Aspen each morning these days due to all the commuters...)
Many, many years ago I moved from Wisconsin to Colorado to ski and I've been living in the Rockies ever since. I have frequented most of the ski towns in Colorado at one time or another and have met many ski bums. In my experience coming to any ski town without local contacts, a job or a place to live and pulling off a winter of skiing is very tough. It can be done, but you'll need a whole lot of luck. If you have one of the 3 at any ski town I would go with that choice. With the internet now it is a lot easier to set things up remotely before you arrive, but be prepared to live in your truck for a while if you just come out here and start trying to put things together.
I had to live outside, in a wood shed, and on people's floors to complete my move, but I do not regret a minute of it. If you are determined to make it happen, it will. You might want to add Telluride to your list. It is very expensive, but has a year round economy with festivals every weekend in the summer, and it's close to the desert and canyon lands for a change of pace. Good luck!