Focus on buying below market value, running numbers first (cash flow, 1% rule), and choosing a landlord-friendly location with job growth.

I am better for knowing what cash flow actually is, the rules on homestead exemptions in my area, etc.

Some lawyers will file ejectment lawsuits and ask for service by publication, but that is not allowed under the rules.

Contact the tenant, remind him how rent is to be paid, and require him to follow those rules.

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

Quote from @Jeff Roth:Monthly rents for mid-term rentals are about 20% (+/-) higher than unfurnished similar long-term rentals.I would not base the income potential for a MTR on a rule of thumb.

It's a great market because you can still find section 8 rentals well over the 1% rule.

Learning how to use the correct tools and materials for a job, YouTube videos and even ChatGPT will help you get through 80% of the problems you will run into.My rule was I would not mess with HVAC, plumbing and electrical Or if it would take more than a few hours. 

When it comes to housing, the FHA rules apply in addition to those of your state/city.

If you have a rule, enforce it.