You're getting OJT right now, but you're about to get burned very badly in a very tenant friendly environment if you don't get the help you need WHILE you're learning.

The key is getting the education, studying it and eventually learning through experience. 

You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.4.

As @Brie Schmidt pointed out if you are the tenant in an owner occupant 2-4 the Chicago Landlord Tenant Ordinance does not apply.You can try to challenge her in civil court (aka hire an attorney and file a complaint) but honestly, I don't think it's worth your time...if I were you, I'd just chalk it up as a lesson learned. 

@Johnery LaurimoreRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder, etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Learn where to look for the date of manufacture and make the seller send you a photo.

If so, how did you learn to manage your rentals well?

You can - and should - say no to this tenant and any future renters.Spend some time learning the law and how it applies to you.

Also, learning about creative financing will be a priority.

She's a jem and learning plus gathering info on how to capture leads, would be invaluable for you!