I grew up not far from Galesburg, in a town roughly the same size. Many of the rural subdivision roads outside of downtown are paved with chipseal [1] rather than asphalt concrete or portland cement. While chipseal is certainly not as nice as concrete to drive on, it is much cheaper to maintain. I remember the road in front of my house getting re-treated every few years. Meanwhile the paved blvd connecting all these subdivisions hasn't been maintenanced since the 1980s, and is turning to rubble. So I personally think the problem (at least for small-ish midwestern towns) is the bias of state DOTs towards creating new infrastructure (paving new roadways / bridges) over maintaining the infrastructure they've already built (there's no ribbon-cutting ceremony when you're just filling potholes). Of course, this mentality only exacerbates the problem.
[1] https://en.wikipedia.org/wiki/Road_surface#Bituminous_surfac...