Of course, this is a personal decision as well to determine if that is the right living situation for your family. 

I currently live in my primary residence (2nd SFH). 

She’s not living in it.

I'm originally from Round Lake, live in Wauconda now, and my office is in Palatine!

It may be tough to find a property manager, and I would expect that you'll have a few additional fees when it comes to the rent by room strategy.I'd encourage you to think about managing the property yourself when living there as the landlord, and would be happy to share some of the do's and don't's that I ran into self managing a few house hack properties. 

I live in the city, so the northern JeffCo is def. closer to home.

They believe everyone has to live inside a home.

There was a tenant that was evicted so there were people living in the house a few months ago. 

I don't live in IL, and I'm by no means an attorney, but let me say this - when you wholesale, you're selling an assignment of the contract, which is personal property.

I'm aware this will hurt my credit for a long time and I am willing to live with that.