@killyourfm It could be that iPods are about 20 years old, which is when nostalgia starts kicking in.
I might not have picked my words quite right regarding Plex. I typically use Plex for all of my media so a lot of what I’d be syncing to my iPod isn’t in a state where I can easily do so.
I’ve been converting video and addding it to the TV app, converting flac files and importing them to the Apple Music app, and getting my audiobook files into the right format and adding them to the Books app.