I kept thinking it would get easier and less nervy as I bought more houses.

@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.

High demand for Section 8 housing.

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

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?

would you rent out your property to a problematic tenant who has a good rental history which means always pays on time with a good credit score. i'm in the process of renting out my house

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.   

How the house photographs gets more eyes on it.