For sidewalks or staircase of this type, better off by demoing it, remove unstable soils, replace with good aggregate base course, then form, place rebar, and place concrete.  

I am not going to pick my pocket for something that is not necessary, say I don't charge much when painting sidewalks vs that of doing a city server room remodel.

This part of the driveway (between sidewalk and street) seems to be a massive eye-sore.

with all the snow that we've been having in Montana it easy to find home based on the if the drive ways and side walks have been plowed.

See Vacant Building Ordinance and registration form at https://ipiweb.cityofchicago.org/VBRCN196039Post, on abandoned building, name, address and telephone of owner and owner's agent for managing, controlling or collecting rents on building so legible from nearest public street or sidewalk. (13-12-125)...but sometimes I see also a yellow sticker on the building. the building does not have a red cross on it. is the yellow sticker indicative of some major damage such as flood, extensive fire damage or structural damage ?

If you have a crack in your sidewalk that is shared property of the city are you responsible or the city?

ETA see #1Those are just a few developments occurring in addition to landscaping (planting trees, etc, improving sidewalks) throughout our area.Hope this helps. 

--I run Numbers with my contractor on the sidewalk.

Many cities/townships/etc. have lot coverage or impervious area (house+paved+sidewalk) ratios that might limit how much you can add, if any.Good Luck!

just from the pics I would call it a total gut job needing a new roof, and sidewalk and who knows what else.