Originally Posted by BeccaPrice
You do have to tell iTunes that it's an audiobook and to remember the playback position, though, on non-Audible files (get info > options)
The problem wasn't having the iPod remember my place per se. It was having the iPod remember my place after I'd reset it, updated the firmware, transferred songs or tried to go back to hear some passage I'd missed.
Relocating my place would have been relatively easy if the file were divided into chapters. But my copy of Underworld
consisted of a single audio file.
Also: I make a point of not syncing to iTunes because I don't like the contents of my music players to be exact reflections of the music library on my laptop.
BTW: congratulations on owning the best-sounding iteration of the iPod. Gens 4 and 5.5 are considered to be the highest-fidelity iPods ever made -- 5.5 being the warmest of the entire series.