I'll definitely have to check out How Buildings Learn, your description sounds great. Both Brand and Kelly have really interesting views on the implications and effects on cities.

There's a great full section on cities in Whole Earth Discipline, and here are some of Kevin Kelly's writings you might like:

http://www.kk.org/thetechnium/archives/2009/01/fossil_cities...

http://www.kk.org/thetechnium/archives/2011/07/cities_are_im...

http://www.kk.org/thetechnium/archives/2011/05/whos_your_cit...