If you do own rental property, here are a few of the problems I've had:It does not include property assets in your net worth in the “retirement planner,” just traditional funds. 

Lastly, after you receive advice from other Chicago area SLH operators & the local municipal agencies that will not only save you time but direct you towards ways to save you money, you are going to likely want to register your business as an LLC with the state and obtain the proper small business renters Insurance policy under your LLC’s name (if its just a 2-3br operation the policy monthly premium  cost will be very low and will shield you as an individual from the very probable situation of being personally liable for the behaviors, damages, & actions of a traditionally high-risk short-term tenant group bc no landlord’s homeowners insurance policy will cover any damages or personal liabilities that will occur when they discover the nature of the operation.

Common area electricity, security lights, etc...an additional callout that I missed.

We will be replacing flooring, cabinets, lights, vanities, toilets, paints, cleaning up the exterior, addressing the foundational needs and more!

Installing exterior dusk-to-dawn motion detector lighting is always a good idea to keep all kinds of vermin off of the premises after hours.

It might be a good idea to have your lease forbid blocking windows with foil, or other opaque items other than curtains or commercially available window blinds (that are not flags or political).Drug dealers, and fake drug dealers tend to block windows so no light can get in, and no Police Officers can see in.As far as flags it's not a proper venue for National flags, and gives you leverage in case someone decides to hang flags offensive to some (such as public display of WWII Axis flags, or socio/political flags) that might be detrimental to your rental business.Good Luck!

If our house took a direct lighting strike, it would likely kill my computers and local backups, but I could fall back on Backblaze. 

Does anyone know a lender that can beat the traditional 20-25% down?

If you are going to light something up, better a smooth Cubano (alongside a snifter of cognac) than a cheap-*** house.      

Finally, this article goes over the difference between a Traditional LLC and a Series LLC and which is best for a RE investor.