@Dave GreenHere are the three options for generating passive income and scaling up a property portfolio: selling rentals and buying a multifamily property, paying off your primary residence, or holding rentals and maintaining cash flow.

Property management involves overseeing and maintaining rental properties on behalf of the property owner.

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. 

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.  

I am not a featured agent and Im closing bulk of my business from BP without doing a heck of a lot, I am just maintaining what I started.  

So I have a rental property that I am paying a management company to maintain and rent out. 

This keeps the liability within the LLC and maintains the separation between personal and business assets.

To prepare, focus on saving for a strong down payment and maintaining a solid credit profile, as both are critical for competitive financing.If possible, look into FHA or conventional loan options for owner-occupied properties, which may offer favorable terms, especially for first-time buyers.