I got an iPod last year and have been really enjoying what's possible with them. Using rockbox opens up a lot of features, especially usb file transfer and flac. I've gone so far as to make my own themes to build upon the old UI
Does rockbox support headphone remote controls (vol+,vol-,play,pause,next,prev) and audio books with chapters these days via extra "audio books" category? I would be interested.
I love rockbox but never quite found the UX to feel quite as effortless as iPod OS. I've tried a few skins for it but all of them end up feeling slightly less slick than stock
https://github.com/D0-0K/adwaitapod