State domicile law should require some legal input on your other questions.

I am a bit apprehensive about accepting them but will research local laws to make sure that I am not in violation of anything.

Both Chicago and Illinois are losing population and are both beyond bankrupt, with tenant friendly laws.

I am not aware of any state with a law that coerces the owner to be held hostage to markups and materials price gouging schemes dictated by the contractor.

I'd seen and been part of several conversations regarding single-color-paint-schemes, and I liked the look and idea of doing it, but after talking with my brother-in-law who owns a successful painting business, and my father, who owned a successful painting business, I decided to abandon the single color scheme.The primary reason behind our choice was what you mentioned.

The more criteria you use for screening the more likely you are to fail to comply with applicable law and the more difficult it is for you to prove you did not discriminate.

Specifically, the law requires the seller to provide information regarding all room additions, structural modifications, alterations, or repairs made to the property since obtaining title if they were performed by a contractor.

When your tenant renews their lease and the rent increases, the handling of the last month's rent can vary depending on the terms of your lease agreement and local laws.

Whether is taking his "course", paying for the self written articles about his success or aka writing "puff pieces", buying fake Instagram followers, sitting on FB marketplace trying to get someone to pay for a house they don't know is condemnable and pay to have DJ remodel it and DJ never completing the remodel,  him spending an enormous time defending himself in small claims court, and threatening charges on  people that don't know law so they pay what he wants.All of those examples came from either my observation, experience, or other peoples reviews of him.The guy rented me a condemnable property.

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.