Look, I use computers all day every day. I've got a lot of music, it hangs out on plex, it hangs out on my phone. Those two things, they handle metadata gracefully within their zones.

Try to take that out? Oh boy.

Trying to load that on an iPod Classic because you're tired of your music listening being interrupted by notifications? Oh boy ^2.

I've got about 9.5k songs, some flac, some mp3 some who knows.

If any of you are planning on playing with an iPod here's some advice.

SKIP ITUNES ALL TOGETHER.

Only use it for restoring an iPod.

Don't let it touch your music.

Manually convert FLAC->ALAC with ffmpeg. Instruct ffmpeg to ignore any video/art streams. Rebuild your library structure to be mostly flat based on artist/album. Run MusicBrainz Picard to grab album art and save as a single "cover.jpeg" in each album directory, then use foobar2000 + foobop(ipod plugin).

You will see people suggest this, think "oh how bad can itunes be, let me try that first".

I'll tell you. BAD. Itunes album art discovery? worse than letting a stoned gerbal pick randomly via where their poop lands.

Don't waste your time. I haven't tried alts for Linux yet, but foobar2000, despite being ugly as all hell does the job perfectly.