We all assume this isn’t a house you’d buy with your own money.

.- Once your time is more impotant to you then the cost of a PMC, you can hire one.2) Hire a PMC to guide you on your first rental and learn from their expertise.- You can buy additional properties and DIY manage those, perhaps leaning on the PMC for any issues you're not sure how to handle on your own.Good luck:)

My previous renters were relocations - either had sold their home and looking to buy another (low inventory so takes a while to find a home to buy) or moving here from another city and didn't know yet what neighborhood they want to be in, or alse building a home and need a place to live until it's completed.

If anything just buy motivating buyer lists or VA until you build your own buyers list.

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?

We mostly buy houses from out of state and are aware of it's challenges but many investors have done successfully, so it can be done.

If you were looking to buy a fixer upper etc..

(and be able to buy themselves a new Porsche with the proceeds)Just more Red Tape!

Investment Info:Small multi-family (2-4 units) buy & hold investment.

Either way this is just a metric to help guide you, with this tenant you already know that they are a good tenant.