[joyjoyjoy]

"The early 2000's were a period of especially low usability for Microsoft's products."

Windows 2000 was actually a pretty stable system, considering MS previous standards.

"user. Over several years, I tried to convince him to switch to Mac OS X, with examples like:"

For me Mac OS was always a terrible system. I was forced to work with some Mac OS during my PhD studies in the lab. Terrible. Today Mac OS is a tax for people who are either to stupid or to lazy to put a decent linux on their machine.