You do a bad job filling the hole. Some hits it and their car breaks. They sue you and the city. The city attorneys successfully push the blame onto you since you're a contractor. You have no liability insurance because you're not a professional because that's the whole point of this thing, right? You're on the hook for the car, a few grand for a medical check-up, and a spurious mental anguish claim. You declare bankruptcy and on the way back from your last visit with your attorney, you hit another pothole and your car breaks. Full circle.