A grid of subway stations with a stop at every block? Sounds rather expensive.
Besides, all attempts to build "perfect" cities in real life have resulted in dull and lifeless places. A certain amount of chaos is necessary to keep cities liveable.
This is exactly Jane Jacobs thesis in the greatly influential book "The Death and Life of Great American Cities"
What Jacobs found is that communities thrive when there's a certain amount of chaos and layered complexity that arises from people interacting withe each other and the environment. That's why places such as Greenwich village and many old European cities seem so vibrant and full of life - they're not centrally planned, they've had time to mature and people have had the possibility to interact with the environment and each other in the chaotic neighborhood.
Agreed, simcity uses a static model. So the rules can be deduced. In reality we don't actually know what the rules are and they are much more dynamic -- i.e. the introduction of the internet, the car, the cell phone, etc. These have impacts on cities, and what people expect from them.
Nature (including what humans decide to do) is very good at iterative optimization. When people do something and it works, they tend to continue doing that.
The reason that overly-planned cities (I live in one: Phoenix) don't work is that it's impossible to out-think millions of people all working to optimize your city in parallel all the time.
Obviously you need some urban planning to assist with things that regular citizens don't understand (utilities), but for the most part, if you let people be, they will build a city on their own.
I think your conclusion (only do the minimum planning you absolutely can't live without) is too extreme in the other direction (compare Huston with Portland or Vancouver).
I don't know what the ideal level of urban planing and regulation is, but I think it's probably somewhere in the middle of the road.
Heck, it's feasible now, but the power consumption and maintenance costs would be fairly insane compared to the plain old cars-and-roads solution. (How often do you see an escalator broken down? Pretty damn often.)
You see more stopped escalators because the escalator is the equivalent of combining the train and the track into the same thing. Tracks don't require the level of maintenance that trains do. Trains can be taken off of the tracks for maintenance, so you don't see the entire system break down when maintenance is done.
I use the rail system in Portland for transportation, and I can say that they fairly regularly have issues with trains on the tracks, or taking down sections of track for maintenance over a weekend.
Besides, all attempts to build "perfect" cities in real life have resulted in dull and lifeless places. A certain amount of chaos is necessary to keep cities liveable.