Personally, I'd start looking in markets you're familiar with, similar to what you said in your post.

In theory, you could QT the property to an LLC in your name and enter into a lease with you personally.

Nice to connect 😎Its in Joliet - Cathedral area I hope to meet you in person as well?

This is the fork where I'm not sure if I'd be good to get some CRE exp and invest in learning about how to review deals for the next 2-3 years, or focus on generating revenue for investment purposes and watch how things are done as a LP.My personality more aligns with networking, reaching out to people, connecting, navigating difficult situations and finding solutions that work.

what kind of investment was/is this  a little more detail may protect others if you think this person is a financial predator.  

Some of the heavy hitters here in Chicago discussed the ADU program with a very nice person from the building department.

Personally, I do not like any strategy or approach that aims to benefit from the misfortune of others.

If you don't look at them before buying in person, you will get burned at some point and regret it.   

Obviously tough to give advice based on minimal info and no info on your personal situation.

Take into consideration that when the person you gifted the property to will have special tax considerations as well