Some guy upgrades his computer through every version of Windows starting with a clean install of MS-DOS 5.0 all the way through Windows 7, via Jason Kottke:
Greetings! My name is Jason Heppler. I am a Digital Engagement Librarian and Assistant Professor of History at the University of Nebraska at Omaha and a scholar of the twentieth-century United States. I often write here about the history of the North American West, technology, the environment, cities, politics, and coffee. You can follow me on Twitter, or learn more about me.