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.
On Windows, I've had pretty good with the old version (v2.x) of XRecode. It's some random dude's shareware project that is basically an FFMPEG wrapper GUI that lets you mass-edit track metadata, download and attach album artwork, and automatically rename files based on the track metadata. I use it for splitting FLAC CUE sheets to individual FLAC track files in my main music library, and occasionally for transcoding those individual FLAC track files to MP3 VBR for my phone/other devices. My music hoarding has gotten to the point where the
Artist > Album > [Track #] - [Track Title]layout isn't quite cutting it anymore because of having remasters, represses, and releases from different regions/countries, so I've gotten to the point where I'm including catalog numbers and UPCs in the metadata comment field along with some bracketed snots for stuff like[2002 Japan Remaster], etc.I still wind up having to juggle multiple convert/rename presets for situations like "various artists" collections and multi-disc albums, but it's flexible enough to work with my "filesystem first" mentality by enforcing some measure of consistency between the metadata and the filesystem on initial imports into my library directory. Too bad the developer completely fucked up the UI in version 3. I've had it for several years and still haven't figured it out -- luckily it didn't upgrade over the top of the old version; it just installs as a separate program.
I also still use Winamp (only as a player, almost always launched from File Explorer shell menus), so I'm probably not the person to be taking advice from in any year past 2011 or so.