Also, NYC is dead. 120 hotels house illegals!

The building stock is like all the other Chicago urban core burbs, so expect lots of 1950's and 60's construction with galvanized pipes, flat roofs, boilers and outdated electrical.

Inspectors always make things sound really bad, that's their stock in trade.

Alternatively, if you're wanting to do something more aggressive, you could consider a balanced fund, such as Vanguard's LifeStrategy Income Fund (VASIX), which is 20% Stocks / 80% Bonds.

It is one of the best examples of City Council and local registered community organizations huddling together to create restrictions intended to thwart development but here they are doing it in a manner which will leave new housing stock in the dust relative to other neighborhoods thanks to terrible design restrictions.

Not all markets are dead right now.

Should I save and pay it off quickly or would the money be better in my pocket or in stock market?

As others said use low money down loan to owner occupy another and reinvest the rest into a another property/stocks. 

If this part of the article is true, why would a landlord go to a unit because the tenant had called to say they killed someone and showed them a video of a dead person? 

For instance, if you want to do 2-4 units then West loop won't work, but Evergreen Park or similar areas might due to the housing stock.