@Will R. I just purchased a single-family 3 min from Breckenridge (Blue River) and my partner works in real estate in Breck. So I will comment only on Breck which isn't the most expensive but is the most visited resort in North America.
Ski-In/Out: I would let this go if you're trying to do anything on a budget and if you're hoping to own the land and turn a profit, forget about it. Land outside of town is going for $100-$200K for <1ac and anything that could be ski in/out will be seven figures as @Rob Withers mentioned above. Build costs are obv variable but $200/sq ft at best (like you know people and have favors to cash in).
You can get decent ski in/out condos for <$300K and I ran the numbers for renting to a year-round renter and it's a few hundred a month shy of break-even, even on a good deal. You'd have to run the numbers on renting in ski season only. I imagine they'd look much better. Also, you could rent to a seasonal resident (people from Front Range often get a condo just for ski season) at decent rents. Not as high of nightly rentals, but you avoid the management fees which, as mentioned, are very high. But you obv wouldn't own the dirt. Would love to see what you find if you do the calculations so please share back to the thread.
I second @Mindy Jensen on remodel over rebuild. Deals can be found if you're patient and creative. I would also be curious about numbers looking at Airbnb/VRBO rates for a single-family and/or condo situations. We'll likely rent our home via AirBnB over the holidays when rates are highest and we're gone, but I'm not really sure what's realistic. I do know inventory gets booked fast in Breck in peak times so even a few miles outside of town, you should be able to rent it at a solid price.
Which Resort?
I might be biased, but if you're intending to enjoy the property yourself during summer, Breck has the most going on. More festivals, more permanent residents, great hikes/bikes, golf. Many other resorts punt on summer. I live here and I can tell you that town is bustling with visitors (our only downtimes are Spring and Fall, really).
Keystone, Copper, A-Basin, Loveland, Vail, Winter Park all are basically ghost towns come summer as there is no permanent population to speak of (A-Basin and Loveland don't even have much infrastructure at all). Would be rather lonely.
Frisco was mentioned and has a great summer and still rents well for ski season even though you need a bus or car ride to get to any skiing (it's central to most of the skiing close to Denver).
Further afield, Crested Butte and Steamboat are amazing standalone towns with great summers and actual towns and cooler weather than Austin for sure. Don't know much about Steamboat, but was just in CB and real estate is significantly cheaper than in Breck. Just keep in mind it's 4+ hours from Denver airport and much less visited in ski season.
I can point you to an investment-focused agent in Breck if you decide you're interested in this area.
