- All four parts would play in iTunes on my PC.
- All four parts transferred to my iPod, metadata and cover art intact.
- On pressing play on the iPod, each part behaved exactly the same way: a brief disk access was followed by the iPod returning to its main menu without playing a sound.
Without a response from Apple, I tried to troubleshoot the issue myself, and started at the seemingly appropriately-titled "Troubleshooting songs and audiobooks that won't play" page. I worked carefully through their algorithm. I deauthorised and reauthorised my computer. Multiple times. I tried recreating my iTunes library—this experience was special, because, without warning, and undocumented on that linked page, iTunes throws out some of your metadata during this process, including Play Count, and Last Played date. Playing fast and loose with user data seems to be a feature of Apple software.
Still without a response to my initial problem report, I began navigating the twisty maze that is Apple's corporatoid website: the feedback form is 4-clicks deep from the front page. On the form page I used at the time (it seems to have been corrected now), there was a very promising link about audiobooks on iTunes for Windows which points to a non-existent page. I related my woe in some detail to the form.
The support droids were stumped. They admitted defeat fairly quickly, which was about the only redeeming feature of our interaction: they had no idea why it wouldn't work, and couldn't add any suggestions beyond what I had tried. They credited my VISA card within a couple of days of my purchase. I guess that counts as a partial success for me, though I'd rather be listening to the audiobook.