Property management is a pretty painful industry similar to general contracting... no one ever calls to tell you how grateful they are that the heat is working lolHere in Illinois, the answer is yes or you at least need to have a managing broker on your team as JW mentioned above. 

License bed transactions can be a real pain.

The city is undergoing massive revitalization and investment.

For them, it was painful. 

And that's what they will do, keep kicking the can, avoid painful realities, inflate inflate inflate.

Realize that the eviction process can be painful but it is also likely that the tenant when they receive the notice to quit will find a solution. 

That's a pain but can be done, though you'll have complaints in Spring and Fall about it being too cold or too hot.

See what their pain points are. 

., 1 year)]Security Deposit: [Enter the amount of the security deposit]Background and Credit Check: [Indicate whether applicants will undergo a background and credit check]Rental Application Fee: [Mention if there is an application fee and its amount]Don't miss out on this fantastic opportunity to make our lovely single family home your own!

I would recommend finding a large developer to learn from or partner with so you avoid a lot of the painful early lessons.