For the longest time I hated the concept of paying tolls to drive down a specific stretch of road.

Nowadays I'm wondering if we would indeed be better off with more freeways under a toll system ... and cities (including your suburban 'cities') being 100% fiscally responsible for their own roads.
If the local politicians cannot handle ensuring the roads are paved and of good quality, they get replaced in the next election. So there is actually more of an onus to ensure no stretch of countless potholes.

In the meantime, since road commissions / contractors / road-workers are essentially all public employees, proper road maintenance just does not happen.