I personally like to manage the risk and take it slow and true. 

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.

Determining whether the venture falls under a service or rental business hinges on the provision of substantial services; for instance, if a bed and breakfast service is offered, it must be reported on Schedule C, triggering a 15.3% self-employment tax.Moreover, personal use plays a crucial role in the classification of the property.

@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.

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. 

A Debt Service Coverage Ratio (DSCR) loan for investment properties is often considered better than a traditional mortgage for several reasons such as: it focuses on the property's income rather than your personal income.

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

Personally, I am fine keeping my deal analyzer separate from the management of the properties I already own, but I suppose there is some value to one-stop-shopping.* Platforms that try to be all things to all people: This category is mostly Stessa and Baselane, both of which offer landlord accounting, self-management tools, as well as high interest cash management accounts.