He's a big, cuddly bear in real life.

Now I invest only here in the Chicago suburbs near where I live like Berwyn and Cicero.

We have a client that owns half the block, so we can set the rates on the higher end, just below what the market can bear.

Are you aware of any real estate investment vehicles that bear interest, are liquid, and are FDIC-insured?

Love visiting Chicago, Schaumburg but I would never live or invest in IL. 

Just closed on a condo unit in the Roger's Park neighborhood of Chicago and I am planning to use it as a BRRRR property.

It doesn't sound like the repairs are really that much an issue from your list there.What you should be more concerned about in my opinion is this part, "Comes with Section 8 Tenant (Mom & 3 kids)"  Now she absolutely could be the best tenant in the world but she also may not be.

@Daniel O'Grady  Like @Wayne Brooks said, whether you’re making a cash offer or a financed offer has no bearing on whether or not you should use an agent.

They've indicated it will have no bearing on ability to pay rent. 

My existing two-flat back in Chicago, along with 25% down from my severance, helped qualify us for multi-family property here in California.