[cousin_it]

I haven't done the math, but my guess is that a pothole might do hundreds of dollars worth of damage over its lifetime, maybe thousands. If society was willing to pay 1/10th of that sum per pothole to anyone willing to fill it, there'd be a lot more applicants. (Though it might lead to people making potholes on purpose, so the payment needs to depend on road health over time, not number of potholes filled.)

[pc86]

Well your last sentence shows exactly why it wouldn't work and so you're not really talking about "1/10th of that sum per pothole" you're talking about, I don't even know - paying random people random sums of money at arbitrary times based on overall road health?

[forshaper]

A map, posted on the municipal or county website. You, a private citizen, bid to fill a hole. The city accepts. You upload a geostamped 'Before' picture. You are given a time window to fill the hole (often at night). You fill the hole. Upload 'After' pictures. Get paid in the next cycle.

[pc86]

You take a sledge hammer to the street a block over. Repeat. Profit.

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.

[forshaper]

Taking a sledge hammer to a street is a crime.

[pc86]

Yes, it is, and this is a financial incentive to commit a crime.