The market value rose from $165 to $187 during my ownership, but rent was flat, shrinking the yield.

Flat or pitched roof?

I own a 4 flat in the Chicago suburbs, but not quite that far from the city. 

Looking to buy my first multi family unit this winter and currently looking at the north side of Chicago. Does anyone have any experienced brokers they can recommend?

I have a project in Chicago that is a 3 flat the I just finished gut rehabbing and it now has tenants in all units.  

@Kendrick Salazar I think a lot of us on BP have discounted the idea that real estate could remain flat for a while instead of going up or down.

Bought a 6 flat, full gut ($700k rehab), rented it out, refinanced, and rolled proceeds into another project.

The roof is has a flat, tarred section and a peaked, slate section as well. 

The market can remain flat.

A contractor may do it, but expect to either pay for their time, or have them flat out say no, due to the fact you are wholesaling and won't even be purchasing the house.Also don't forget to account for all holding costs, lending costs,closing costs, etc when you tell your buyers about the "profit".