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.

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

I live in AZ, left to live in CA for 14 years, then moved back in 2007. 

They had a career (possibly dual career family), lived below their means and invested.

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.

(FYI, We are trying to build a small (5 to 6 properties), high quality portfolio in the next 5 years, planning on putting 25-30% down)The investment opportunity in question is a new build, single-family home with a 3-bedroom, 2-bathroom layout, accompanied by a 2-car garage, located in the neighborhood of Wesley Chapel, FL.

For us, we found a good deal on a change machine being sold as part of a car was demolition, so that seemed like a better option. 

Currently living in Madison but looking to invest in the Milwaukee area as prices aren't as crazy it seems.