It's really surprising how many cities, even small ones, had some type of trolley system in place that got overrun by the automotive movement. And now can't figure out how to insert a good mass transit system into one that's made for cars.
Also, a song that came to mind in seeing this image is Dire Straits' "Telegraph Road".
Most of the value was probably with the brand itself. Which he then tossed away. Genius.