Nice restaurants in a ski town will likely be one of the major limiting factors. Vail has some pretty decent restaurants, and usually during the off-season they have some type of deals like 50% off wine, 3 course dinner for $35-45 (and it is 3 courses from the the regular menu, not some prix fixe), etc. A couple of the places I have been to:
There also aren't really going to be many theaters out in the resort towns, so that may be tough to find...
I wear 42R, and got the gray overcoat in 42. If I had sized down, it wouldn't fit over suits, sweaters, etc. If you plan on wearing the coat over anything (good chance you will), go for it in your size. Also, 38 appears to be sold out, so your decision just got easier.
Hey now, that case was thrown out, and the DA was disbarred and filed for bankruptcy. Plus, the accuser is now planning on representing herself in her murder trial...http://www.newsobserver.com/2012/10/08/2399243/mangum-wants-to-represent-herself.html
Colt & Gray in Denver is pretty good. I don't think it would meet your wine list criterion, but figured I'd throw it out there. They have a decent offal menu and it's definitely worth visiting for the bar alone if you end up moving out this way. Kevin, the head barman is fun to talk to about pretty much anything cocktail related (or not related). Let me know if you end up out here as I'm generally in town on the weekends.
Of the others...
I had In-N-Out for the first time two weeks ago. Definitely didn't live up to all of the hype. The burger was decent, but not the godsend to rule all fast food burgers that Californians make it out to be. The fries were simply awful. Shake was good, but it's not hard to make a decent shake.