If you go in willing to learn you will be on the path to prosperity.  

As someone with a managing broker’s license, I know how rewarding it is to guide others through their real estate paths while continuing to grow your own investments.

You have been given some great advice here, because even in a war zone.. we have a housing shortage in this country and people need a place to live. 

I liked real estate so I got licensed, worked on a bunch of different RE strategies, started developing and managed to get myself stretched thin very quickly again, I basically made the pendulum swing way too far and had to consolidate again to find my path.

With your experience and a clear goal to build wealth and transition into multifamily commercial properties, you're on the right path.

The property was well-located and priced under market value, offering a clear path to profit without needing significant renovations.

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

Non-payment of rent is always the path of least resistance to get someone out in a somewhat timely manner.

Do I give up access to transportation, restaurants, cultural activities, doctors, emergency medical care, religious and business activities, vet care and maybe more, to live in the country on my ranch or on the beach in a beautiful country, or do I keep access to all those things and live in the city? 

As the 3rd largest MSA in the country it's hard to generalize the Chicago market as it's actually over 100 different submarkets when counting the 78 communities in Chicago property and then adding in the various suburbs, including in and around Naperville.