Chicago cap rates are actually much higher then other comparable sized cities.

https://www.renterswarehouse.com/rental-listings/39331Now on this listing an important feature to it is the size, not just of the property but the lot, the feeling of big, space, and of semi-secluded.

The house is also furnished with a solid wood no spring couch, and a solid wood round dining table, and a king sized bedroom set in the master.

This would greatly increase the size of your next downpayment.

What do you bring to the table and what do you need from a partner?

In most cases due to the transaction sizes, there's very little margin for these 3rd party vendors (particularly brokers, property managers and contractors).

Don't leave this option OFF the table. 

Honestly, I don't think there's a one size fits all or a right or wrong way to invest in real estate.

I am wondering what it takes to deliver a higher customer experience, equivalent to receiving a warm wash towel at a restaurant table before you eat. 

This is a fine needle to thread because at this size, you very quickly start competing with high net worth individuals who are seeking summer homes.