Maintenance at at PM company or one of the big hedge owners like AH4R, leasing at apartment complex will teach you a lot about applications, fraud, leases, collections, evictions. 

The city made me conform to their exact permit application process which was burdensome and frustrating.

You will be asked to disclose this during the application process, and not doing so is concealing a debt and would be fraud. 

@Joe Norman Those were the big 3 I figured would help the most, but I think wasn't sure how much actual applicability they had as a business owner/investor.

Piling on...all occupants who are 18 or older (or legal emancipated minor) should absolutely be required to make application. 

.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

It is super important to thoroughly vet house hack applicants.

There are various applications that allow landlords to collect rent, manage payments, and disburse funds.

We accept all applications and in the case of section 8 the only real time we don’t is if the numbers don’t make sense with market rent vs HUD standard.  

As a fellow West Aussie who's now living in the US, I can tell you this forum and most of the training/courses you'll see online regarding multifamily investment isn't relevant/applicable in Australia.