Since many of the suggestions on this thread are for nonfiction, I am going to put in a plug for literature.
I would like to point to one of the most subtle and flexible literary minds, the internationally acclaimed Jim Crace. Jim Crace often writes about transitions, where the traditional meets the technological, and the consequences of that meeting. His use of the English language and sense of character is so engrossing, I have experienced a sense of malaise upon finishing one of his works, wishing that it hadn't ended. Two of his books that may interest list members:
In _The Gift of Stones_, he takes us into a village of stone-cutters at the advent of the bronze age, struggling to continue their way of life as they are pushed into the next era.
In the novel _Arcadia_, he traces the symbiotic relationship between a city and its leading citizen, and the way that each shaped the other. Those of you who share the view that a city is a sort of organism will truly enjoy this novel.