Very nice write-up... I remember the days when Winamp was King. I even got an Infrared receiver for my PC, and had it working with Winamp. It was pretty sweet being able to fast forward / rewind / shuffle, etc... with a remote. This was in the Napster days I guess about 7-9 years ago?
What bothers me is the hysteria surrounding Apple. They make a white remote with 4 buttons and suddenly it's "incredible design" and "pure genius."