[spaceprison]

I was thinking something similar.

Carve the geography into small population density based chunks

Identify boundaries like Bisecting Highways, railways, Rivers, mountains, etc.

Create boundary informed population chunk clusters.

Identify features Food Industry Schools

Find the shortest road based path from each bounded cluster to each feature.

Create convex hulls that enclose bounded population chunk clusters of the target population size and paths to features.

Rerun after every census.