It's a carrot, not a stick. It's designed to spread the digging.and repaving costs around so the work is cheaper. It's more that the city knows it's doing work in an area, digging up the road, so they tell all the utilities, hey if you are thinking of doing work on Main Ave, we'll be starting work on September 3rd, if tell us now and can get a crew out before September 21st, you won't need to pay to excavate and repave.

Emergencies are emergencies.

Maintenance is largely required to be scheduled, so utilities cannot wait until things break, they'll be required to perform maintenance/replace at pre-established frequencies. So we might not know when in 2030 the road gets torn up, but we do know it will be, since maintenance is required that year on infra X,Y,Z. Scheduling of the precise dates is then done according to the window.