City Stripping : building historical road layouts from todays data

Street map of Buenos Aires 1895 (plano de Basch)
Source: Wikimedia Commons

For at least one year I have been thinking about the best way to create vector streetmaps for different historical periods for the same city. The basic principle is simple: take the existing street layout and remove what is new! Essentially, this presumes that any current vector data will be more precise than digitising vectors from old maps.

I have even given the process a name: "City Stripping", but in practice my attempts so far have been less successful than I hoped. I think that  I kept too much existing OpenStreetMap data in my first attempts, because in practice I found it easier to re-trace the old data (as here for Tartu/Dorpat).