Also does anyone have any references for realtors in Chicago who are experienced in condos and rental properties?

You will want to consider having the tenants sign a new lease agreement if you believe that's necessary based on the existing lease agreement.If you're referring to your agreement with the property manager, make sure there's no additional costs or hidden fees.What is the best way to officially inform the tenant about the management change?

I'm sure I'm missing items, but in a word, yes, this would be useful.  

I guess I'll just let my dream of being paid for referring go as I'm not looking to be a real estate agent.

We have more maintenance requests but usually for smaller items.

Since you mentioned Mapple heights keep in mind that area will have a Point of sale inspection or POS as a lot of people refer to it.

COSTS:  I would look at any-and-all things needed to run an STR including items that are often done by owners--for example, property management.  

Make sure your lease stipulates its a "shared property" and list all the rules to make sure they toe the line, garbage, one vehicle(where parked), noise, no personal items in yard, everything you can think of or choose/whatever.

It's always a plus when you can get your property valuation increased and the tenant pays for the new item, just so long as your downside risk is mitigated, too.Good luck!

I see you are in the Austin area so if you need a good attorney let me know I would love to send a few references.