Years ago I read How Buildings Learn: What Happens After They're Built [1] on a recommendation, and I wasn't disappointed (oddly enough, it seems more programmers buy this book than architects). The book goes into depth on how buildings are adapted (or not—Frank Lloyd Wright's buildings [2] are notorious for their inability to adapt, in addition to the leaky roofs) by successive tenants.
Now, the author of the book, Stewart Brand [3], has uploaded the documentary based on the book to Youtube [4] (link via Jason Kottke [5]). For a brief minute and a half peek at the type of content, there's The Oak Beams of New College, Oxford [6] (one of my favorite bits from the book).
[1] https://www.amazon.com/exec/obidos/ASIN/0140139966/conmanlaborat-20
[2] http://www.franklloydwright.org/
[3] http://sb.longnow.org/SB_homepage/
[4] https://www.youtube.com/user/brandst/videos
[5] http://kottke.org/15/07/how-buildings-learn