Yields in Kansas City are very high.

What Chicago City inspection report did your realtor find? 

If your goal is to offset your mortgage with a house hack then Lowell would be a good bet, but if you're looking for a longer term appreciation play then the areas closer to the city would be better, although the offset from cashflow may be lower than what you're looking for.A good step for you would be to dig into specific areas more as @Lien Vuong noted above.

Ok, well now STRs are regulated in that city, and that same income approached value plummets since the home can only be rented as an LTR.

Well, I heard about this tactic, and was so excited to try it out until I tried looking through Jackson County’s public records portal here in Kansas City.

Do you want to get into what can be a years long battle with multiple parties, including our darling city council, until you get to move into your home the way you want it?

If you don't do that and the neighbors complain like it happened to me, the city will knock on the door to see what's going on and give you like a $100 per day fine which I paid.

Never noted on city plans. 

But this is Rare.. you cant compare most low value areas of cities in the mid west or Rust belt to Charleston SC.. 

Do you have a specific area/neighborhood of the city where you are looking to househack?