Researchers at MIT have been using computer vision to look at Street View and map urban change over time. Read more about it on Maps Mania. The original paper from MIT is here and a map of several US cities with their results is here. Look for white dots on the maps to see ‘before and afters’ of various locations using Street View.
Detroit has seen dramatic change, gradually falling to one third of its maximum population from 1950 to date. Unfortunately, Street View and overhead imagery only cover the most recent changes, but even so, significant changes can be seen.
Aerial imagery, Highland Park, Detroit, showing houses removed between 2002 and 2016.
Street View of Highland St, Highland Park, Detroit, showing houses decaying between 2009 and 2013. The houses have since been demolished.