As a broker, you’ve already got a strong foundation, which will give you an edge in finding and structuring great deals.Since you're in Chicago, have you considered house hacking as a starting point?

@Derick Jennings Without knowing more about your situation, I'd likely recommend a house hack, a strategy I wish I would have known about when I got started.

Is there no one else of your religion in the area looking for housing?

High demand for Section 8 housing.

I don’t think the tiny house would get you there.

But to answer your question, House canary is good for rent rates, zillow is a good tool for property data and for seeing what is for rent for how much, sales comps etc. 

We manage 300+ units, I've flipped over 75+ houses in the past 3 years, and I currently own 28 long term rentals.   

The house is offered to the buyer at the ARV price, and we explain how we plan to rehab the property and its worth after repairs (ARV).The end buyer has to make a commitment of at least 10% of the ARV, provide proof of funds, and other documents required to list the property on our website.

How the house photographs gets more eyes on it.

@Phillip Austin someone who obviously should not rent but buy themselves a brand new house. what was their previous place?