I love that these homes are in class A neighborhoods, I have seen this strategy work out for investors before but they were at least cashflow neutral. 

Plus I'm in a very HCOL so the math for short term rentals would not work out.  

Apparantly that didn't work out for them either as they sold all their properties a couple of months later.

I schedule my work out so that way its manageable on my part and 95% of complaints are not urgent.

But if you bought your properties correctly, it will work out.

With enough properties, the savings could justify quarterly visits for inspections and lump-sum repairs.Best of luck and I really hope things work out for you. 

You can be nice, but professional, and work out an amiable move-out.

I understand that rents will go up over time and my mortgage payment will pay down the principal, but it seems like investing the $1.43mil into rental properties and/or a low fee US stock market fund may work out better for me. 

These old houses built 70-90 years ago seem to never break once I work out all the kinks.

In the end it will all work out.