So I activated my real estate license and jumped in looking and comping.

While it is also true that Chicago leans tenant friendly, you can mitigate a lot of that risk by investing in areas that have a stronger tenant base.

If you like a market, just get a base hit deal there and start spending time at the property getting to know the house, the market, and local vendors.

For example, I used AirDNA for a property and came up with $54,200 annual income, Pricelabs says $24,600, and my estimate based on the property my in laws stay at is $32,000.The income is the hardest for me to estimate, even using enemy method. 

I would recommend finding a more altruistic source of information before making decisions based on some information provided here and on the podcast in particular. 

I should probably start a new thread here but I thought I would jump in an ask as I am following @Sean Williams question.

Based on what I'm reading here I would focus more on Airbnb/Vrbo.

On a fix and flip you may want to up your minimum profit desired before jumping into to a deal if the market is shaky, but as has been stated people still need houses regardless of the market conditions. 

Two AF bases there, which is usually a good sign for the rental market.  

Lastly..Gang seriously.It is frustrating how much proof I constantly need to post yet so many of you are so invreddibly stubborn so see what is right infront of you, and make decisions based on emotion/opinion, instead of Proof, Data, evidence.It truly is up to you.Want to keep struggling?