I have a similar story, but with a different outcome.. My mother was running windows 95 on a old PC, and she had some trouble. I looked at it, decided I needed to re-install, and told her that I wanted to put Ubuntu on it. There was a bit of worry if she'd be able to figure it out, and I told her yes, and also strongly suggested that when she asks for my help, she should be willing to accept my recommendations.

Voila, Ubuntu installed and a brief, "wow, I'm actually running linux now?", and she was happy. Firefox, Thunderbird and OpenOffice FTW.

Corporations with archaic IT operations procedures will be difficult, but the Windows 98-neighbours and mothers of the world need to start using Ubuntu.