The mother has continued to pay the property taxes and has kept them current.

or not worth the extra money?

Do I need to contact the city of Chicago to have the water shut off or is this something I can do myself? 

To all aspiring house hackers and those aiming for a single-family primary to hold it as a long-term rental, what are your biggest frustrations likely keeping you from jumping in the game? 

It was listed on the MLS and was right down the road from us.

I have gone ahead with painting Navajo White for all the walls, and Ultra White for the trim and plan to use this color scheme throughout all the units eventually.

Quote from @Jerome Wiley: Can the landlord ask a perspective tenant how many adults will reside at the rental property?

I'm underwriting an 80+ unit property and it seems like the purchase price is too high compared to the market.

I don't have the money in my account for a down payment currently but have a plan to within the next few months.

I'm borrowing at the rate of ~7% and 7% is a great return to me, especially with the stock market near all time highs.