@Miranda LeMaster If your agent can not offer you a good commercial option, then you are working with a personal lines agent and you may want to think about making a change sooner than later.Ideally you want to have 2 separate insurance programs.  1 for your personal and 1 for you business/commercial exposures.  

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

@Jay RitchieI came across this website which I think could help you: https://www.leadsafechicago.or...If you qualify for the city's programs, you may be able to get it done for free or at a discount.

I think communication is key.

When you leverage money personally, I think it makes more sense to invest in appreciating markets

@Jacob Caffee, I think what John is getting at is: on BiggerPockets, there is a mid-term rental forum that would be the more appropriate place to post this request.https://www.biggerpockets.com/forums/925

@Allan KapoorI think you're being smart, but here's what I don't get. 

Did you buy this property site unseen?

The contract he signed with them was extremely pro seller, and I think he figured he would eventually foreclose/evict them and we would never know.The guy was a joke, fraud charges were filed by the DA on him, but going after him for any money would have been a waste of time.

The process can be more intensive than you think.