Shouldn't major foundation issues be something that should be reported in home inspection at purchase?

Will permits or zoning be a major issue and etc.

I am sure that you would think that the Turo contract would help with that, but seeing as you are providing it as a service in addition to your STR, I can see issues if there is a problem.Plus you are offering significant services with that rental and that would change your tax situation.

I’ve been trying to solve this puzzle for a while too and the issue I keep running into is more so not being able to claim Short Term Rental income until a year or two later.

I agree with @Nathan Gesner that the migrant issue is fueling the fire on the affordable housing crisis, more people needing them has to drive scarcity. 

I also have a limited power of attorney in my contracts to allow me to handle any other issues that arise.

My house is on a corner with an empty lot next door, so it was not an issue for me.

I've been deliberating over the same issue (long-term rentals vs. medium-term rentals) and am inclined to invest the extra effort to manage a medium-term rental, given the appealing additional cash flow it promises.

One of the tenants has been causing issues with other tenants.

What I often see being a mistake is people ordering a cost segregation study before speaking with their accountant to see if it would benefit them on their return.What a cost segregation study does is analyze a property further to identify assets that be classified with a shorter asset life than 27.5 or 39 years.The issue when getting an 'estimate' from a cost segregation study company is that they are not accountants(more specifically not your accountant).