Resources are optimized relative to their current values. Medieval construction was often labor intensive because it was the cheap part compared to materials. City housing got disrupted by a new technology, cars that made additional cheap real estate more available for use.

Central planning can theoretically avoid some growth pitfalls "skipping to the end" but in practice it has often had limited success beyond zoning promoting the obvious - high traffic areas are good for retail and often annoyance to residents. I am no expert but it seems predictive design performs best with planning.