Trust but verify.Through deal analysis, you will be able to establish your own buying criteria and recognize the bad, good, and great deals.Education is a lifelong pursuit.

Last, recognize that the rental market is soft in the City. 

What we were looking for is verbiage on how to write tenants’ lease agreements noting the contract is between them, the tenant(s), and the Owner, but recognizing our company as the property managers.  

Leasing with HCV | The Chicago Housing Authority (thecha.org)Here is some information for the Chicago Housing Authority Mobility program.

But one thing that you may want to think about is you are not legally qualified or trained in Fair Housing discrimination or property code laws and you could actually say something that could get you in legal hot water just because you don't know the local, state, or federal law if you do not feel comfortable with the company that is managing your asset then I would suggest another conversation with that company to put some type of triggers or kpi metrics in order so that you can make sure that they are doing their job but going to the tenant turned it into a he-said-she-said whenever there's a problem and what you're doing is you're bypassing the authority of the property management company and not even sure if legally you're saying or doing the right things.

I recognize you from the RHA website.

Its a duplex with a ADU in the backyard(its zoned SFR-2, up to 4 units are authorized on the lot). 

Eventually, you will be able to recognize the bad, good, and great deals.

Hey I'm partnering with someone for my first deal (I'm way excited) and I'm wondering if we need to create an officially recognized partnership that is registered with the SOS to do that or if we just sign a contract stating how we'll operate and share profits etc.

Check with a local title agent and ask if they're authorized to issue a policy w/o exception for the prior owner's interest if you get a deed.