We went from buying light rehabs to buying major foundation and mold issues to make numbers work until even that did not work anymore.

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

The issue always boils down to equity.

I read this as someone using a short-term lens to focus on a long-term issue. 

Any legal issues I should be aware of in this situation? 

Newton's law of tax: What goes down must come up.Everyone enjoys the sweet benefits of bonus depreciation, but what happens when you sell?

You may run into issues with re-tenanting and it may take longer than you expect or cost more.  

We have two main issues that I will outline below: HeatingTwo heating systems in the home.

Usually b/c if the deal is so amazing, the money is rarely the issue, and b/c those people that do have the money thus get to cherry pick for the 1 in 10 or 1 in 15 that is the MOST amazing of "amazing deals." 

However, in this situation, it appears to be a pattern rather than a one-time issue.