|Street map of Buenos Aires 1895 (plano de Basch)|
Source: Wikimedia Commons
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).
State of the Map 2014 in Buenos Aires provided another opportunity to try this out. Fortunately a small number of historical maps were available on Wikimedia Commons. I chose two: