My wife grew up in Norwood Park and most of her family still lives there. 

San Antonio on the other hand is only an hour and half away and is the same distance/time as it was for me to go from where I grew up in Woodstock, IL to Chicago- so I’m not opposed to investing in SA.

In regards to market to invest, the Midwest is a great market for cash flow but the quality of life can be lower compared to the coasts/warm environments (that’s coming from someone who grew up on the ocean but moved to Ohio for school and stayed for rental investing).

I raised rent on them once already from 2k to 2400 few years back but rent as steadily grew since then.

I grew up in Montgomery county myself. 

local boy  grew up in Cupertino went to Palo Alto as they had the best public schools in the state was our primary reason. 

Challenge was finding the right cliental at first but rapidly grew with nurses after providing a good product.

If I was in your shoes and had time to kill but money sitting there I would invest it in index funds so it grew until I was ready to pull it out to invest in real estate. 

Your line " I mean really why even be here just to work and die." is how I felt as I grew in my career.

@Jonathan KlemmI grew up in Bucktown!