I suspect this is partially due to Chicago's strict laws regarding security deposits.Fellow landlords, where do you fall on this issue (especially you Chicagoans)?

They offer some of the best terms, however they have some strict requirements as well. 

Tenants are paying all utilities so expenses are just taxes and routine maintenance.

If your properties are strictly for rental purposes and not used for any personal activity, all expenses for those properties should be reported on Schedule E regardless of your decision to itemize your schedule A deductions.

I'm typically "by the book" and someone who likes to follow the rules strictly.

I searched online and found a website strictly for registered agents for $50/year. 

Thanks If you go conventional and do not occupy the property and buy strictly as an investor the qualifications and guidelines are more strict.

Since it sounds like landlording is apart of your plan, I would make sure you are familiar with the pretty strict landlord laws in the city. 

I have a strict no evictions, no felonies, must make 3x rent, and have the ability to pay deposit and first month within 48 hours which weeds out a lot of people I wouldn't rent to anyway.  

Freedom from my strict upbringing, the military discipline, school rules and grades, corporate bossman.