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As it stands, I live in the master bedroom, I have had 1 long term tenant that has been with me since the purchase and the other 2 rooms have been listed on airbnb and have found some temporary tenants through mutual friends.

@Dustin Horner you should be contracting maintenance work and creating a preferred list of vendors as @Phillip Austin has recommended.The first person you hire to help you should be to handle what you LEAST like to do yourself or has the greatest time savings for you!

This listing is off the MLS.

Then when you have a deal, you send it to everyone on your list who has expressed interest in potentially investing with you.

Awesome jobIf you are interested in some local Chicago Meetups here is the list BP has:  https://www.biggerpockets.com/forums/521-real-estate-events-...I have a FULL LIST OF ALL THE CHICAGO MEETUPS that I will send you! 

You need boots on the ground to see who lists flips and who lists dumps.

So, when we call the landlord the tenant has listed on their application, we can ask questions to uncover fake landlords.

I would list now but do a 6 month lease.

The people who never ran properties in B or C area always scream about how bad idea it is but you can make an incredibly profitable listing in those if you know how to manage it.