I hate it too, it really doesn't like my Audio books. I have a lot digitised from my old cassetts.
The CD audio book is treated like an album so every chapter is an individual song. Shuffle that and make sense of it won't ya LOL.

Every so often I have a go a finding the missing files on my computer then get them into iTunes, then I have to make sure they get in a proper order and I have other things to do with life. Why it just never found them all, I dont know?
I have to have it all as Music as I can't work out how to get it into Audio books. It seems to find all the duplicates on my back up disc as well so if I am not carefull I would have double everything on the iPod.

It is great if you just like pop music and download it from iTunes.

The problem is that, who else does large drive MP3 players anymore?

I have an iPod 80 gig under sufferance right now. Lucky I got it cheap second hand and so I put up with it.

Happy I have not put any monies into the Apple Pie. Chris smile

No 18 in the Hall of fame smile I have simple tastes; I am content to settle for the best:
GIK monster bass panels, rear wall. QNAP TVS 471i3. Roon into DSP5200SE via 210/ 218 zone... Explorer 2. Bluesound Pulse 2, Mini & Flex. 596v1, 518, Foxsat HD, Sony BDP, Pioneer 5090, 2 Chromecast's for LRB videos. MS200 to F80 for a Roon zone