I've been using iTunes for years — originally because (in 2001) the other MacOS X mp3 players sucked, but now that I'm on my third iPod (
first,
second) I'm more or less locked in.
Most of my iPod listening is in the car, or on airplanes. I also take it with me on walks, and recently got a cassette adapter for the
built-in stereo in my kitchen. Over time, my general iTunes/iPod setup has gotten increasingly complicated — with a big leap this morning. In this article I'll attempt to document what I've done, and why, both for your amusement and so I can recreate it in the event of a catastrophic data loss.