Posted March 19, 2011
While doing some googling on Windows and marketshare, I ended up stumbling upon a site where they performed an experiment with almost all versions of windows. Their goal was to test the upgrade path capability of windows from Windows 1.0 to Windows 7. As seen in this video using VMWare, yes it's indeed theoretically possible to install MS-Dos 5 and Windows 1.0 and then proceed to upgrade in sequence all the way to windows 7 without needing a clean install. In fact, certain settings and folders that were created in windows 3.0 were still present in Windows 7. What ever your feelings on Windows or Microsoft in general, it's still pretty damn impressive.
http://www.youtube.com/watch?v=vPnehDhGa14
http://www.youtube.com/watch?v=vPnehDhGa14