I also committed to fixing the sidewalk and external repairs to make the street look just that little bit better, as well as not requiring any major modifications to the building - paint, flooring, tile, etc.

There is nothing in place if there is damage from say a car accidentally running into the house, hail damage, someone tripping on the sidewalk, dog bite or if there is major damage to the house that is not fire related. 

I cut a deal with the bank to replace the sidewalks and some outdoor lighting with proceeds from closing.

@Leslie Voegtlinhttps://chicagocode.org/13-12-030/The owner of any building having residential units designed or used for two or more family units or designed or used for sleeping accommodations, other than family units, for more than ten persons shall post, or cause to be posted, in a prominent place in a common area of the building accessible from the public way, or affixed to the building so as to be visible from the public way, the name, address, and telephone number of the owner, his agent for the purpose of managing, controlling or collecting rents and any other person managing or controlling such building.I haven't seen a specific size listed/required, just that its reasonably large enough to been seen from the sidewalk (public way).

You are not in such bad shape if a balcony rail breaks and your tenant dies hitting the concrete sidewalk, but if you are hit with some sort of sexual lawsuit, retaliation,  harassment, or discrimination then you are getting sued, personally, not your insurance company and you have to pay the attorney fees from your pocket to defend yourself unless you have inclusions in your policy for those types of lawsuits.

In Janesville, the city will issue citations for the sidewalks not being shoveled.

Minnesota area so lines are pretty deep usually in basement, and yes i am looking to hook onto city water not sure if they pre set up the line to the yard or if im pulling from street which means breaking up side walk and trenching 4 ft down

Look for the water meter at the street or sidewalk for your property.If the leak is BEFORE the meter at the street the water department is responsible.If the leak is after the water meter it will be YOUR responsibility to fix the line.

A little peeling paint, wobbly handrail, cracked pane of glass, uneven sidewalk, etc will cause the appraisal to fail. 

No sidewalks, streetlights, curbs, etc. required if a land sale.The reason is that if selling over four acres here, then you are selling land/a farm, not a lot.