Other municipalities have addressed these kind of issues by declaring them a "Local Improvement". That means that part of the cost of the major repair or replacement of the street or sidewalk can be assigned to the property taxes of those residences fronting onto the sidewalk or street being repaired or replaced. It is called a frontage tax. Taxpayers pay a couple of dollars per foot of frontage per year for a period of years or they are given the option of paying it off outright.
This is quite common in a city's or town's older residential areas where the streets and sidewalks have seriously deteriorated. The cost of streets and sidewalks in new areas are paid for by the developer and added on to the price of the new homes there.
Taxpayers along the street being repaired or replaced have the right to cancel the project by petitioning the municipal council. This is what happened along Seventh Street a few years ago.
Local Improvements are a way to go to get some of these projects done sooner than the village could otherwise. The village has to wait for street improvement grants to be issued by the province before such work can proceed. At our present rate, all existing street and sidewalk issues would be completed well into the 2030s! And that's not counting any new issues which might pop up!
Let me know what you think.