Re: Options
It's a while ago now, but I used to have a 5th gen iPod video (my daughters until it was chewed by the dog, so after replacing hers, I repaired the chewed one and kept it for myself), which I managed to quite successfully manage my music library using Amarok on Linux. Syncing with iTunes was not something I did, but downloading music onto my laptop however I needed to (CD rip, Amazon Music etc) and then re-indexing Amarok and exporting the music to the iPod worked fine.
I still use the same setup with the exception of putting the music onto my Android phone rather than an iPod. I also manage an SD card for the car the same way.