For your question, as far as I understand, the city of Binghamton doesn't allow STRs, but a lot of people do them anyway.

In cities with static or declining populations, the existing housing supply typically meets housing demand.

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.

Yields in Kansas City are very high.

., just call the county/city and get the skinny.

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.

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?

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.

What Chicago City inspection report did your realtor find? 

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