I wouldn't kick them to the curb for that.

Do they need curb/gutter/sidewalk?

When you drive other houses in your comps, what other creteria you are also using to do visual inspection except for house condition, curb view, street and proximity?

Curb Appeal is basically Number 1,, if the building parking area (no junker cars) trash area (neat and clean), grass cut,, flowers, shrubs trimmed.If it looks good it will rent.. 

Before you stage,call a local real estate agent and ask them to come over to see the property and give you an honest critical opinion as to the way the house is showing.Tell them you are not hiring them to sell it and just want an honest opinion.They are going to want some money for their time so offer a hundred bucks or so.They hopefully will show you why it is not getting offers like poor decoration choices(too cheap or ugly),Poor curb appeal(bad choice of paint and landscaping)or the neighborhood itself is worse then you think.Bathrooms,bedrooms,and kitchen may not be big enough for most buyers as well.

as you know  it must be in writing.. verbal means nothing.. you can play this to your benefit.you edify yourself as a professional using full transparency instead of some sleazy wholesaler that won't disclose anything  LOL.. your professional  I believe personally you act like one and kick all the wanna be competition to the curb... when I used to deal on the street level and the buyers would tell me they had some other offer from some other wholesaler I would just absolutely cremate them and 99% of the time I got the deal.pointing out all the weakness in the wholesalers contract.

Chicago is too big of a city for people to just leave...I know some high crime areas are seeing people leaving, but currently lot of stuff happening to curb crime in 4 primary high crime zips in Chicago..so hopefully things will be better.

She doesnt have much money or credit for that amount of a house at least or prob for any house at all.Its bringing up the emotions that you are kicking me to the curb etc since she built up this airbnb business that works for her  (( also have a reverse 1031 I am trying to get in the timelines for)

Two menopausal, single women, what a delight.

Personally, that house has so much curb appeal right now, I'd want to move in, without having seen the inside