@Derek Morris

I've always been surprised when looking at markets for my STR investors that Granby (and Winter Park and Fraser, etc.) don't do better. Their prices aren't much lower than other mountain or ski areas but their revenues don't match.

But in your situation, if I had to rank buying in a place that allowed STRs and buying in a place that had slightly better numbers but was less secure regulation-wise, I'd opt for the former. If this is going to be your retirement place, it has significant meaning, then that matters most to me. 

And the areas you're looking at do work in terms of laws. Grand County and Lake Granby both allow for non-owner occupied short-term rentals. And that is increasingly rare for Colorado cities/counties. Gilpin, Clear Creek, Summit, Routt (Steamboat Springs) all either don't allow them or are way over their caps. 

Oh, and the actual town of Estes Park has a cap on the number they allow, but on the rare occasion, a property will come up that has an active STR license, and Estes is one of the rare cities to allow existing license holders to transfer the license to a new owner. (With most cities, the license is for the owner, not the property and is forfeited upon sale.)

Alma is likely better in terms of numbers. You're as close to Breckenridge as you can but still be in Park County, which currently allows for STRs. (Though Park is also looking at regulations.)

I'd get with a good agent who follows STRs and Airbnb rules. (Subtle self-promotion there.) And good luck! Buying a vacation home is a little scary but also very exciting.