What would you do in Chicago market?

[Greg Kusnierz]

Looking at a single family home with an in-law apartment in the basement. We would live in the top floors and Airbnb the basement. 
would need the income of the Airbnb to make it a viable house in the long term. 
it would be our first investment property

The mortgage would be over our budget but with an Airbnb income could make it work. Checks a lot of boxes for our family to move in as far as location. 

Is it wise to move in and be entrepreneurial or is my emotions getting in the way of my judgement?

[Brie Schmidt]

I would join the FB group "airbnb hosts Chicago"

The city is cracking down on the ordinance rules.  If it is a seperate unit it is my understanding you cannot list it without a commissioner's adjustment and would likely need to hire a lawyer to try and get it approved.  Lots of people had rented out another unit in a building they owned and got their listing removed