I had a friend with an MA in urban planning from University of Illinois (I think). He said that Detroit was pretty much used as the example for what not to do in most of his classes. To be fair, planning for explosive growth is always difficult.
I'm not sure that it's so difficult. I've sat on many (volunteer) commissions, boards, etc., for State Highway, the County Executive, etc., here in Montgomery County - an ultra-liberal/socialist D.C. suburb. What I've found is that the planning was done very well in the beginning. Reasonable roads, etc., for the development. Then the moron politicians cancel the roads each time a community group shows up yelling NOT IN OUR BACKYARD. Also, the council members are always wanting more campaign money (developers have plenty), so they go and re-zone parcels of land for high-rise buildings (many cars) without making sure that the roads are adequate to get the cars to and from the buildings.