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.

I know everything may not go as planned but the principle and goal is the same.

And thanks for the adherence to principles intended to keep BP free from “disguised” bias, @Scott Trench.  

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.

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. 

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. 

You can't buy stocks for a discount just because you don't buy them at the NYSE.

What I also enjoy is when people put out articles with contradicting view points and in six months or a year point to the - "see how correct i was", well yeah you placed bets on both red, black and green so you were going to be correct because you bet on all options.There’s a true story about a person who, during the late 1950s wanted to make money selling a stock market prediction newsletter, but had no verifiable experience or track record.