Please check out this great blog post from Romanian mappers.
 
Ever since I saw great ItoWorld animation Year of Edits I wanted to make my own version. This look like it is possible, as mapguy has clearly demonstrated.
UPDATE: Ciprian aka Mapguy has made tutorial explaining how to make OSM progress animation.
 
So in order to make this work they made git repository for planet file and that is how it is possible to get a history for some town or place, because git repository keeps all changes ever made.
 
So in order to make your own animations you need to have your own planet.osm git repository. That is the first big hurdle :(
 
I hope that OpenStreetMap project creates an official public git repository so that anybody can get “history” for his town/place.
 
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