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

I doubt you will have to do this, but some areas of the country are nutsy...

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. 

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? 

Avoid Kaufman county, that's good ol'boy country there.

I also live in a VHCOL living area and if I lived in another country with very low costs I could possibly live off my cash flow, not happening in the USA for me. 

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

But, did you know that your beautiful country of origin Mexico also has plenty of exciting real estate investment opportunities?

OOS flipsOOS rentalsOut of Country investing.....but the returns in Cleveland and favelas in Brazil are amazing....how often do we see those posts.

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.