Another issue is these homes have standard 15-30 year loans in my personal name ..... so that is another issue ! 

You have code enforcement issue in one of those cities and they do not know you, your life is not going to be easy meanwhile the person who has been there for 10 years and knows the inspectors families name will have a very different outcome than yours. 

I am personally staying away from STR‘s and MTR‘s because of its inconsistency.

My 2 cents would be that since it is your personal property that your CPA is right but im far from a tax professional!

I cut my teeth in the war zone-ish eastside Harvard Place.

I, personally, have mixed views on this.  

Sometimes people who are comfortable managing the details of a job will hire a less skilled person to do it knowing they can get a MUCH better price and a "decent" job IF they themselves stay on top of how the work is being done.

Often ADU projects have comps where they compare the ADUs to little office spaces, personal yoga studios, etc.

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.