Looking forward to someone doing the same sort of thing with other OSs.
Like other commenter said, Windows/MS really goes all the way for backwards compatibility.
Also the settings would have only been preserved in Classic, but that's to be expected I guess.
Such quirks are partly what would make such things interesting.
Slackware goes back to 1993, is there an earlier Linux distro still in major use? (looks like there isn't - http://upload.wikimedia.org/wikipedia/commons/8/8c/Gldt.svg).
It might be more interesting with Linux to follow a WM?
I wouldn't mind seeing the same video idea with Ubuntu. Somehow I don't think it will be long before a copycat does this :)