In the winter, the sidewalks need to be plowed after each storm...

I agree with everyone. being local, I get to walk up to the property, see the sidewalk, see the roofing and warped floor boards from the window, etc. 

For that reason alone, the Association should carry liability for the "common areas" which are the streets, sidewalks, greenbelts, etc. and D&O because you can still be sued by a homeowner for a decision whether it's negligent or not and fidelity (just in case one of your upstanding board members is pocketing association money when no one is looking).

Recent cement driveway and sidewalks. 

There are also families hanging out on their front porches and neighbors greeting each other as they pass on the sidewalks.  

If my tenant does not clear the sidewalk, and someone slips falls and sues, I guess they will likely come after me anyway regardless of what the lease agreement says.

Sidewalks built?

Since the old structure can no longer be grandfathered in, some locales also might require you to upgrade the infrastructure and adhere to new zoning like setbacks, building height, add sidewalk$, install tree$, retaining wall$, etc

Meaning when he sees restaurants either popping up or converting putting out small tables, turning into sidewalk cafes, he starts buying.

Will you need new sidewalks and driveway?