My hope is to buy in B- to A- area, prefer a small 2-4 unit (they don't seem to be very easy to find).

Basically, i think all i need to close the door the Bedroom to the kitchen area, add an exterior door, add kitchenette, and possibly add its own electric panel.

Was it better cashflow, newer, or bigger/more units?

Maybe look at 2-4 units atleast here even in the trendy nice parts of chicago 2-4 units still cashflow positive. 

You don't want to start a relationship to learn about storage units and then find out they only invest in single-family homes.3.

I'm living in a home, that I've gradually renovated to some degree, initially for the purpose of establishing a rental unit.

Ask how many units they manage and how much experience they have.

Fannie Mae: "The income approach to value is required in the valuation of two-unit to four-unit properties . . . 

I am leaning towards split units as well. 

- 3 units are occupied by seller’s close family - All units are on month to month basis- All units are significantly under market rent- 1 unit pays on the 15th of the month- 1 unit has not yet paid for Match 1st even though my information has been provided to them twice- I have no applications or old leases1.