[notahacker]

Suggesting Windows 2000 gave him "no idea what modern operating systems were like" was pretty jarring too.... far from being "obsolete" it was only four years old at the time and from the perspective of the average user not stuck on a 486 lacked only a bit of UI gloss compared with the state-of-the-art XP. If nothing else, you'd expect he might be impressed at the progress the internet had made since 1999