I am just trying to navigate when am I being too lenient, to a point of being taken advantage of and when I am being too strict to a point of running a tenant off.  

I had a roommate like this for my first house hack and she was great at first, but I didn't stay strict on certain rules and things got stretched out more than they should have haha. 

They have strict requirements.https://www.chicago.gov/city/en/depts/bacp/supp_info/sharedh... 

It is very strict.

Safely I believe you have to have a minimum of 10 units to sign up, and Waivo seems to be raising prices while simultaneously getting more and more strict on denying claims.

You can specify blackout dates when the property is not available for rent if you wish to use it personally during certain times of the year.Legal and Regulatory Compliance: The management firm will ensure that the property complies with local laws and regulations concerning rental properties, including obtaining any necessary permits and adhering to zoning laws.Maintenance and Repairs: Property management firms often take care of routine maintenance and emergency repairs, ensuring the property is well-maintained and ready for tenants or guests.This arrangement allows you to enjoy your second home for part of the year and generate rental income when you're not using it, with minimal effort on your part.

Hi Ropo, Are you looking to house hack or strictly investment?

They apparently have strict rules about what the owner company can be involved with. 

Buyer beware of course but these are folks I routinely use and trust.

There will be a lot of proven people here who demonstrate that you can totally self manage an out of state property.It really will depend on you, the market, the property, and a few other factors some of which may be out of your control.I would not look at PM strictly as a cost, there are a lot of good local PM's who can add value to your property.