No need to invest out of state, when you are in one of the best places in the world to invest in real estate. 

I worked as a firefighter so I got the building construction from that background and then the transaction and numbers I got with working within/alongside investors that were in the business doing the stuff I wanted to do.

The won't insure you or they will jack up the price considerably. 

I found houses that had not been well kept up.

Yes, long-term rental clients sometimes don't want short-term rental next door to them, but you are the owner and landlord and set those expectations up front so it's on the table before they lease.

How much are you having to pay the management companies?

Posted twice for some reason.  

@Travis TimmonsI had the same reaction as you did, but I held off on posting since I don't yet invest in STRs (I'm all LTR so far, and looking into my first MTR).Buying an STR "to offset income" makes me nervous as well...

Quote from @Wade Wisner: Hey Jay,  Thanks for responding to my post. 

Might be a little bit down the road for me, but that is for sure dream that will come true...One Chicago's best features is the lake, which I'd like more access to.