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

I'm also building up a stock portfolio as I have neglected that over the years (but glad I did to invest in RE). 

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. 

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.  

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

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 shouldn't by a "DST" or a "stock" just because it's for sale. 

@Chris Miller history doesn’t repeat itself, but it does rhyme.I remember 2006, and how the fed was engineering a beautiful soft landing and everything was great and home builder stocks and banks and investment banks were THE stocks to own because all the data was pointing to a rosy future.The only data source you would need is the yield curve.