Many of us believe that “Windows upgrade” is buggy and doesn’t work well when you upgrade from older to newer version. We have often recommended a clean install but this video is here to prove every one wrong — A Man uses VMware to emulate old hardware and install DOS to Windows 1.0 and then upgrade it to all the subsequent versions, all the way upto Windows 7. And surprisingly, it worked.
The adventurous guy didn’t include the Windows ME, a big failure. The journey is documented as a 10 minute video examining the upgrade process a Great recall for all Windows versions.
Twenty Years of Backward compatibility
Before starting systematic upgrades, The Secret of Monkey Island and Doom II were installed to test DOS functionality in each version of Windows.
The results of the experiment are pretty amazing–the games worked in every version of Windows but Vista, which had clumsy DOS support, and problematic everywhere. Twenty years of backwards compatibility? Whoa!
As far as installation times are concerned, they peaked with Windows 98 and Vista–So we conclude, its possible to upgrade from Windows 1 to Windows 7 without much trouble.