On the other hand if there are sidewalks we usually handle clearing them because as you said, the town/city will fine the owner if it isn’t done. 

Someone slips and falls at property A due to poor sidewalk maintenance on your property (negligence).

Street that fully complies with city spec, curb gutter, side walks, off site improvements of city frontage, to name the big ticket items.  

@Kyle Davis They ask you.They have people who go by insured properties.Some insurer will also tell you that certain repairs need to be made even after years of coverage, things like sidewalks, railings and things visible on outside of property.If they ask, or you sign a false statement, then have a claim, they can disallow your claim. 

They are some big boys too you do not want to mess with.One time I was at  parade at Atlanta on the sidewalk. 

Received a letter from the city (Columbus, Ohio) stating a complaint was lodged that the sidewalk in front of my home needs repaired.

For example, the city where I invest might post a warning about the lawn not being cared for, sidewalks not shoveled, trash pick up not handled properly.

Are there people slumming around on sidewalks and porches?

Grading issues, water leaks in the basement, water dams, leaky roof, drafty windows, boilers, furnaces, garages, retaining walls, sidewalks, failing plumbing, unsafe electrical, peeling paint on siding, etc....

They suggested I speak to HOA about putting trash cans near the sidewalk & bike path.