Starting smaller is fine, but the unit has to be spa like or you will likely fall victim to pricing wars or get lost in the booking sites algorithms. 

Look at Listed properties, open houses, for sale by owner (FSBO), wholesalers deals, any on site auctions you can find, and look at as many deals other investors own that they are willing to show you. 

I wouldn't be investing in any new city without spending a lot of time on that site first.

Go to crexi or similar site.

I still have a little more than three weeks left Yes, and the DIY sites are mentioned in the blog post I previously linked.

The area near the ski resort has few off-site accommodations and no hotel.

If the investors is not well versed in these three areas, they will not be able to successfully utilize the tactics and strategies that have proven as wealth accelerators by numerous real estate investors. 

Airdna is the best site to get STR rental numbers.

However, there are numerous ways to CREATE investments that have 15% or more cash flow AFTER repairs and allowance for cap ex.  

I would check with an attorney or CPA on it.EDIT - Check out Scott Royal's site - https://royallegalsolutions.com/what-states-are-permitting-s...He used to be on here quite a bit but I haven't seen him in a long while.