The risk/reward remark you made is a reason why someone MIGHT buy those deals, see #1 from my post.

They manage every aspect of your rentals not just accounting. 

We love all aspects of real estate from our vantage point as real estate agents, and from the perspective from investors.

Good to know about the legal aspect of payment timing.

Yes we do have many properties that we manage ourselves so we’re ready for that aspect of it.

We self manage our other properties and are pretty good at the channels and the marketing aspect, there would still be much work to do in finding the right contacts to make it possible; I.E cleaners, maintenance, preferred vendors etc.

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.

Multifamily DSCR Loans, or DSCR Loans for 5-10 unit properties, combine the best aspects of DSCR Loans (30-year fixed rate, easier qualification and underwrite, low down payments) for properties that traditionally were ineligible for that type of financing.

My best advice is to thoroughly research debt until you’re very comfortable and familiar with all aspects.  

But they all suffer from the same over-arching problem that Quickbooks has, which is that they aren't tailored for our business and can't handle some of the unique bookkeeping aspects we have like needing to split mortgage payments and import transactions from a property manager.