And for sure I highly doubt those that teach the common wholesaling techinques are not up to speed with all these new laws in all the different states..

Will they "check themselves" from bad behavior when they see a professional company with professional services, legally reviewed lease, etc. managing their day-to-day?

Can add a in-law suite for lots of value.

I don't know the law or eviction procedures in Saint George, Utah.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

It is a great company.

However, just because I don't agree with it doesn't mean I am in favor of the Government being given additional power to enforce additional laws and restrictions that infringe upon our freedom.

Also any tips for automating this as much as possible and how to protect the property financially and property management would be appreciated.I ALMOST understand the rental arbitrage strategy if building a company scaling with say 30 + units and looking for high short term cash flow.  

And I think a lot of companies will realize that productivity is generally higher in cooler climates.

The law allows you to charge for ALL cleaning, including trash removal.