@Cody Cook. As @Tim Emery implies, in the actual resort towns a lot of the real estate has been well picked over and ROI's tend to be fairly low. I see two main reasons for this. A) Location location location - there are only ever so many places that are going to be walking distance from the chairlift, and so investors are willing to take a lower cap rate with the expectation it will be more than made up for in the end with appreciation. B) You are often competing against other buyers who have no idea what ROI or Cap Rate mean. They just want to be able to tell everyone they have a place in Aspen/Vail/Telluride.
I cant speak specifics for other areas but here are a few examples for Telluride. It is important to realize that everything in town is only walking distance away, the town is surrounded by both NFS and open space, and there is a limit on how high you can build. The least expensive 2/2 condo is 659K. You can probably only expect a 3.5% ROI if you short term rent it fully managed. With that said, I just bought 2 hotel rooms that get a 6% cap 100 yards from the lift - they are 1980s and the crappiest rooms in town. They average around 210 nights per year at 140/night average or thereabouts. More nights than anything else in town because they are the cheapest. They are not sexy, and so point B above is not really a factor. Management takes around 35-40% of gross so you could trade a bit of time on Airbnb for a higher return.
As an investor, we are always looking for value. We often get caught up in the numbers though and sometimes forget there is much more to it than just the cash on cash return. If that's all that was important we would all just buy in St Louis or Michigan. That's not likely the same house you would want to go stay for 3 months in the summer though!
I guess, because of that, my best advice would be to book yourself a tour of Airbnb's throughout the state. The whole state is great, but diverse, and all the towns are different. I for example don't like Vail as IMHO its essentially a glorified truck stop, sterile, with none of the old cowboy charm of a place like Breckenridge, Crested Butte, Aspen or Telluride. To get the best 'Value' find the town that works for you, then the investment that will work for you.