In WI the seller hires the title company to pull title and it is customary to close there, but I hire my own and we close at my title company.  

It has to be a strictly arm's length investment, and most self-directed IRA custodians will require that you hire an unrelated 3rd party property manager to ensure it stays this way.  

Gist of the idea is you develop your marketing advertisement (think: car magnet), hire a driver who is already actively driving around (Lyft, Uber, etc), and have someone (or many someones) marketing your company while they drive. 

Anyone have experience with hiring a contractor to solve something similar?

Large apartment complexes frequently hire property managers without requiring a license because they are employees of the company.  

It would basically consist of managed risk, lots of diversification, and constant diligence on managing your portfolio, or hiring someone who will.

I do my own property management, but you will hire a property manager.  

I have my contractors license and would hire out most of the work.  

If you are looking to hire a new property manager for your real estate what are some of your top questions you would ask them to see if they are right for you?

This is not an endorsement as I haven't used this personally, but I've heard good things from those who used Upwork and hired VAs from the Philippines, as you can find those who speak perfect english.The tips I was given was to really screen out those who are detail-oriented and can follow a script really well.