Seriously, though, the advances from Windows 95 to Vista are less about improving the "tool" and more about improving the experience of using the computer. I don't think you can really call a computer a "tool" anymore, anyway. It is the communication, entertainment, and productivity center of many people's lives. It serves far more value than a hammer or a pen. It has the ability to morph into practically anything. Back in 1995, when the real value of a computer was still somewhat ambiguous, people called them tools because that was the closest metaphor to a a familiar paradigm. Today, the computer is the paradigm.
The argument this guy uses is kind of stupid and reminds me of the short-sighted, extremely stubborn attitude of the most geeky people I know. He doesn't like Internet Explorer 4, so he refuses to use an operating system based on IE. While IE 4 was a terrible internet browser, it served Windows pretty well; using the idea of back and forward buttons for browsing files/folders is still used today in Linux, Mac OS X, and Windows. Sure, Windows 98 sucked at it, but that's exactly what Windows XP improved on. (Arguably, Windows Vista improved on this as well.) That's why people upgraded.
In the end, by using Windows 95, he is just torturing himself. He might gain pleasure from the novelty of writing stories like this one and getting strange reactions from people, but in the end, his experience of using his computer is just... terrible.