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

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.

Will permits or zoning be a major issue and etc.

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. 

For you investors that have ordinary income to write off let me tell you the greatest secret to minimizing tax liability, Cost Segregation.When coupled with zero down seller financed purchases the numbers get crazy.Th...

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

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).

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.