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.

You will likely meet some real estate agents that would be more than happy to sign you up as a client for a somewhat extended search (to be your agent when you are ready, to get you signed up, send you potential opportunities, etc.)

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.

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

Even my personal prop to live in I find and negotiate.

The only reason you would want to try to find a market to flip houses in that isn't the market you are living in is because you can't afford entry level homes in your market.

@Ravi KaruturiHello RaviI hope your enjoying the weather down there in Texas, I don’t personally live there but I would love to jump on a call and discuss your situation.

My family and I would live in one of the units in order to be able to do this, and there would be an additional 3 units in order to get the full amount of the FHA loan.