@Krista Goodrich Great question! And one that I have both passion and experience in and have commented on in a few other posts. Lot's of great thoughts thus far. I'll build on what's been said with a few of my personal thoughts.
There are a lot of factors that come into play. Personally, I believe that you can make something work in any market if you know not only WHERE, but also HOW to look at it. Takes a bit of creative thinking and sometimes you have to flip things are their head. Look at it differently than others with a bit of a disruption mindset.
In my opinion, much like BRRRRing or Flipping, where you can't pay retail in order to make it work...the same is true with mountain/ski area properties. Every once in a while you find a diamond pop up, but these are rare. And when you can find something it either is a wash from a cashflow perspective or barely cashflows. Nothing wrong with this if you are an appreciation investor. But my personal strategy is for some form of cashflow. So when you analyze markets and properties, especially in the mountains of Colorado where I live and invest you will find, as you have described, that nothing seems to work. A bit different from the midwest markets that I also invest in where cash flow is a bit easier to come by.
What's next? Well you can definitely monitor a market or two waiting for something to inevitably pop up that probably barely brakes even. Or you can flip things on their head and look for ways to create equity/cashflow. Definitely takes more effort. So what does this leave you with? Like my BRRRRing/Flipping comment, it often leaves you with either looking at/for properties that no one else wants because they are trashed (and therefore you can often get them at a discount) or building. Both options leave you with needing to find and hire local contractors/trades unless you are planning on doing the work yourself. Personally, this is where I have found success. It's harder and more stressful, but most things that are worth it are.
A potential third option is to send out mailers, typically to out of state owners. I have found property this way as well.
Other factors to think about are costs. How can you keep expenses down? This can be a big issue in mountain markets. Most of these markets have a deficiency in skilled labor. Or even labor in general. As a result, everything costs more. So one thing to think about is how you can strategize around this. e.g. If you want to build, maybe don't build something on site, build it off site (pre-fabrication) and bring it on site. It's a lot cheaper to build in Nebraska or Minnesota than a ski town. Contractors/Trades...is there a market close enough that you could find someone skilled and willing to make the drive to wherever you are rehabbing or building at a more affordable price?
I've personally leveraged these approaches and techniques and have found success. I'm sure there are other thoughts and approaches from others here on BP. I recently finished building two ski houses near Winter Park. I long term rented one (because the size is common and STR income is on par to slightly less than long term renting) and then I short term rent the larger one. I was able to pull out all of my money I put into it to finish the build. I actually pulled out more than I put into it. I have a bunch of equity still in both properties. And they both cashflow. So worked out well. But definitely was a lot of work. More so than a traditional purchase.
Given the crowds at resorts and the growth in desire for the backcountry, I've been working on an Off-Grid Backcountry Ski House property. Still working on access so it's a slow burn, but making progress.
Happy to chat more if you'd like, just reach out.
Best,
Michael