You have to check people in, respond to requests, complaints, arranging cleaning crews, handyman, lawn / pool maintenance, walk-throughs, responsible for accounting etc.

Table 1006.2 of the Chicago Building Code should cover most basement units with only one exit.The Municipal Code of Chicago gives and exception that allows ceiling heights for Dwelling Units to be 6' 8".Look at the exceptions below.14X-4-402 ARRANGEMENT AND MINIMUM DIMENSIONS.14X-4-402.1 Minimum ceiling height. 

The executrix should not get involved with the sister about allowing the sister to purchase the house at a discounted price, at a long-term for sale by owner arrangement. 

A clean and uncluttered house allows your prospective buyers to mentally put themselves in the home and decide on their own living arrangements without input from the home seller and certainly without bumping into family members or household pets while they are in the home.2.

Does anyone here know how the utilities arrangement is?

@Gary Lucido  I suspect cutting a check to a buyer out of your commission is a violation of licesne laws I know in ORegon and CA you can't do that.. your limited to how much referral fee you can pay its usually a bottle of wine and some flowers.also out our way attorneys charge 500.00 and hour.. so no savings there.but I like getting buyer brokers arrangements and getting cash up front.. sure will separate the tire kickers and time wasters.. but then again I can see them whinning and accusing you of not actually spending that amount of time on the project..seems to me a buyers broker arrangement with a reduced fee would be appropriate way to handle this.AGents go into real estate to GET OUT OF WORKING BY THE HOUR...

She had some arrangement with the previous owner.  

Can someone please explain what types of insurance would be needed to be properly protected with this type of ownership arrangement? 

Once covid hit, I was glad that we had made this arrangement with one of our tenants. 

You could arrange an energy audit.