Yes. Stewart Brand should need no introduction to readers of HN for his many influences on high-tech industry, but I'm always telling friends about How Buildings Learn: What Happens After They're Built,
http://www.amazon.com/How-Buildings-Learn-Happens-Theyre/dp/...
especially friends who study architecture.
Would recommend "The City in History" by Lewis Mumford. Great read about how cities have formed, died, and some renewed throughout history.
Look at this map of lower Manhattan from the 1600's to today: http://www.racontrs.com/stories/nyc-land-reclamation. Look how, aside from land reclamation, the basic street architecture has changed little since the mid 1700's.