What would happen if we divided cities into neighborhoods of 500-5000 and had each neighborhood finance their own infrastructure, like in the 13th c.? My guess: we'd see tons more dirt roads, cobblestones, far higher density and far more rail. Or more right pic less left pic. 
No neighborhood would vote to spend millions yearly to build and maintain roads for the sake of trucks, even if it meant groceries would be 5% more expensive than at the the big box stores outside of town. Anyone who proposed such a plan would have to be a raving sociopath.
"Whenever something is wrong, something is too big" — Leopold Kohr. Let each neighborhood chose to deal with their infrastructure as they see fit. A neighborhood with high unemployment would do well to cobble all their streets. Labor intensive but maintenance cost virtually free.
The way we build and finance streets today is "with large upfront costs and then regular maintenance to be paid from the economic benefits of the street." Spot the problem in that model! It is a textbook ponzi scheme and we are running out of money. Hence, ballooning public debt.
