I have loaded books on CDs into iTunes. Many of them have dozens or even a hundred tracks on each CD, and a book might be 10 or 15 CDs long. These audio files typically have a name like Track 1, Track 2, and so on, there are no differentiating titles, up to 25 or 99. So when I first loaded up a book I'd have 15 tracks called track 1, and 15 called track 2 and so on, and I quickly discovered that iTunes could get confused about the order of these apparently identical files.
With audio books I generally have no problem listening to them in iTunes. On an iPod it's another story. I was listening to a collection by Neil Gaiman, with 70+ chapters. On my iPod they were out of order, but not in iTunes. I took the book and merged all of the chapters, adding chapter markers. It was easy, but, sorry, I don't remember which program I used, maybe QT pro, Garage Band, or Audacity. It played correctly on the iPod that way, and I could select chapters. It's possible, no, likely, that since I didn't RTFM for the iPod Touch, I might have set it on Shuffle by mistake.
I haven't bothered to tag things on my computer. My file system works OK for now and I don't want to add another layer when files already have metadata embedded anyway.
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