As a disqualified person to your IRA, you may perform very basic and limited administrative activities, but you may not personally benefit nor may you inject value into the IRA via the provision of goods or services. 

At a high level, it appears that you just need higher yielding assets to which you can perform like-kind exchanges.

Your issues with your GC not performing as desired could potentially be smoother by implementing contracts/agreements that are signed and professional.

@Brian Garlington believe it or not, he actually told me he does it very casually.

After some years of reading about real estate, I started to develop some general guidelines to follow when it comes to correctly measuring performance in real estate, especially since I wanted to compare performances of other investments such as stocks, bonds, etc. 

I’d find their listing on Airbnb and see how it’s performing.

Unless you have specific items in your lease that they need to perform there is nothing you can do about how they keep their home. 

If you were to perform a cost segregation study, you could depreciate the assets included in the purchase that have shorter useful lives much more quickly which helps increase your cash flow of the property.

@Yoselin Pearce I'd encourage you to look into school zones, and target high performing school zones!

if so, its a winner...even if not, the one that is performing better covers the difference....you could always trade it, but what would it be worth in 25-years?