Already called the police and they successfully removed him and I secured the property but im concerned that he keeps showing up when the unit is ready to resale/rent. 

@Kristin Vegas - If you are buying in Chicago proper, be sure to become familiar with the landlord tenant ordinance which is specific to the city. https://www.chicago.gov/city/en/depts/doh/provdrs/landlords/...There is a good stock of multifamily housing just west of the city if you are looking for a more suburban feel with better schools and policing while still being able to get to the Chicago city center within 15-20 minutes. 

Also the only way to (maybe) get these inquiries off your personal credit is to repeatedly ought-right lie to the credit bureaus, and as I have found out, one of the bureaus absolutely will not remove the inquires without you supplying a police report... 

That creates a civil dispute that police may or may not assist with until you go to court over it. 

:) Great self-managing comes for well-organized systems, polices, and procedures.Any advice on ways I can move forward with my goals?

I bought a ring alarm system that can be monitored and nearest police station and fire station close by.

If they are a vagrant, try to get the police to trespass them.

I don’t know how they would enforce it, over time the Rent Registry could play a part in policing.

In my eyes this is harassment the police don't drive by my house as much as she does.

Keep in mind most cities you cant touch these folks... maybe the pendulum is swinging back to logic and protecting the innocent landowners. yea also this country needs more logic/rationality and military/police presence more.