@Jacob Dalton, I'm going to have to agree with Jonathan Klemm (sorry, couldn't tag you) & @Brie Schmidt -- you can definitely be a successful landlord in Chicago with the right team in place.  1000's of investors do it every day. 

Registration and Financial Considerations for the Second Company:Is it possible to register the second LLC on the property (as part of the 50%-50% model) if it does not yet have an EIN (Employer Identification Number)?

I was going to tag Will like I always do but he already did it so that's covered :) I am in a college town and have rented to a lot of college students.

The $40 000 USD price tag was not worth what we were given. 

Or maybe it was just some tax identification number, I don't remember clearly.

I call this dumb debt: Quick note; the deferred sales trust can save a failed 1031 exchange( cost zero to have this option, nor does it take any of the identification property positions) (It's wise to always have a back up plan)More on Dumb debt.

For the owners who just look at you with a price-tag, they generally do not understand the business.

You'll be tagging transactions throughout the year with categories that fit the Schedule E so when tax time comes (if you stay on top of it) every deposit and expenditure will already be categorized and it's quick to create the Schedule E and/or run P&L reports any time you need to.

Yes, people see the low price tag on these self-service options (there are a few more being marketed here, not going to put them on blast) and ignore CPA guidance to go with in person option and it is now coming back to haunt them.

It's not just about slapping a price tag on stuff; it's about effective communication and making sure you get those green bills in your hands.