If you are thinking about having someone driving around to photograph everything frequently, yes. But a couple of cars outfitted like the Google Street View car

If you are thinking about having someone driving around to photograph everything frequently, yes. But a couple of cars outfitted like the Google Street View cars, each given a section of the city to drive every other month or so is very feasible. You could also put cameras on any public transit vehicles to keep photos coming in from vehicles that are already being operated by city funds.