Luckily both sites collect the taxes for our place.Our little town did implement a 1% tax that I have to pay separately.

It may be more helpful to put some of your specific questions right in a post or separate posts.

It keeps each set of books separated and allows for quick analysis of each building.

We have a partnership entity, so it has to file separately and needs balance sheet accounting.

Mainly via students and separate room rentals.

Two of the units have their own W/D. 4 others share a separate W/D so it isn't taxed very much.

Doing this (renting both entire house and single bedroom rental) allows us to be able to tap into 2 separate target audiences and accomodate those singer travelers, couples coming to the area that would normally scroll past our listing due to size/cost. 

I am a rental property investor but i hate making things complex and the last thing i wanted to do was create a separate bank account for each property..yikes.

If you find a separate habitable space, the ADU cost is significantly less.  

. - You've got some pretty solid information above and concurrence that it shouldn't cost nearly as much as you thought, but on a separate note, I'd like to understand your situation a bit better.You are currently just looking for a Chicago property to purchase and asking the quit claim question in preparation for closing?