Sometimes I go past an old looking building or see some traces of old signage on a store and wonder what they used to be, especially when those traces are hard to read or obscured.
I have good news: It exists! http://retrographer.org/
A lot of them are unrecognizable, but here’s an example of a good one: http://retrographer.org/photos/4215
The bad news is that’s a bit limited. It was the senior project of a CMU student in 2010. It only exists for Pittsburgh, Pennsylvania. If you wanted to make one for another city, though, I think you could contact the creator, ask for the code, and then recruit people to get a ton of photos from another city’s historical institutions, and then crowdsource geotagging them (which is what the guy did).