I haven't tried it before, but have been thinking about checking into it.  

I recommend a simple spreadsheet to check your math and it will make it simple to adjust each year.End the complaints.

It helps you find reliableproperty management partnerships and gives you everything you need to makeconfident hiring decisions: Expert Matching: Match with professionals who meet your criteria Extra Assurance: Licenses, experience, ratings, reviews, and more that can be cross-checked with BiggerPockets members Bonus Content: Receive an essential interactive workbook: “How to Interview Property Management CompaniesHere’s how it works:  Enter your market and what you're looking for Instantly see top matches and their qualifications Connect with only those you want to interview Bonus! 

There are also a bunch of free tips and tricks for optimizing your listing that can help with search rankings. 

Check out the Chicago Creative Investors Association run by Jane Garvey.

Zillow has a lot of property data, including from third parties against which it might check that data.

(This is the part that Im not sure is dumb or not) For two years while I'm living at home rent free, if I'm able to charge $2.1k each unit for rent, I would be left to pay $600 out of pocket to cover monthly payments.

We offer a free customizable POF on our website when you sign up with us (at no obligation). 

Feel free to DM me.EDIT: Sorry I just realized this is 3 years old!

I checked the lease created through Zillow that does not show up any option for reletting but what I am aware (done it few times when one of my other property was managed by a property manager) is tenant could pay reletting fees (typically one month rental) that allows property to be re-listed.