And always check social media for red flags and I agree with Vince, always meet a person.  

This approach might speed up access to funds without waiting for June.

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

We make people take photos of themselves holding their ID and then I also meet them in person for the showing - at least for my units on the NW side of Chicago.I've never heard of these testers, but I am not surprised. 

The interest rate on a HELOC or Heloan may be better than the personal loan. 

If you ever decide you want a more passive approach, there are turnkey companies out there that handle everything for you.

Fast forward 2 years his landlord mentioned in passing he might sell the property; I was the first person on his mind.

Mediation is a process in which the parties meet with an impartial person who helps to resolve the dispute informally and confidentially.

I'm a guy approaching middle-age, living in Chicago.

If you make the person an LLC employee you can get around it, but partner does need to be careful.