Either A) you need to want a ski Airbnb/VRBO for the personal use of it but not the investment aspect of it or B) you need to be okay with some of the areas within 45 minutes of the ski areas that are totally open to short-term rentals and where the numbers are better.

@Hannah Potter Here are the things that many CPAs support their clients with:Understanding tax impact of short-term vs. long-term vs. flip before you buyWhich entity structure is best for goals and investment property typeTax and compliance on LLC or S-CorpHow to transfer property out of personal name into LLC (hard to buy 1st through entity)Ways to optimize taxes throughout the yearHow best to set up accounting to track income and expenses (doing this late is a mess)Feedback on property management systems, accounting systems. systems, etcEstimated payments to avoid penaltiesKnowing when to file and getting things in on timeMaybe a few things I missed, but this is the high-level ….. if you can get answers to the above questions on your own, plan, and file your own taxes then you can avoid the expense of a CPA.

As that will at least help folks that you reach out to know that you are a real person, with a picture and professional bio.

Me personally, I would save up a little bit more to at least 30K.

There are several popular programs out there, but personally I like Baselane because it's specifically for real estate investors so all your transactions will fit into the Schedule E you're going to need at tax time.

One person's unique could be my ordinary, and vice versa. 

CGL coverage will cover property damage, personal injury and  bodily injury but not many other issues that often arise, particularly during construction. 

Personally, I would look at the equity and would let that be my deciding factor.

House hacking will also give you some personal "property management" experience.

As that will at least help folks that you reach out to know that you are a real person, with a picture and professional bio.