I have used iTunes off and on for around two decades and it has never been a great or even mediocre experience. It was always bad. The author is fondly remembering a time which might never have existed.
I think a lot of the Music.app issues stem from it being what looks like a SwiftUI/Catalyst app more than anything else.
Here was my train of thought on reading that:
Who voluntarily uses iTunes?
Who voluntarily uses iTunes on Windows?
Can you watch movies in iTunes on Windows?
Why would you ever want to do that?
Blacking out other monitors on full-screen? That's a pretty novel idea, I've never seen that before. Apple would never implement such a cool feature on a competing platform.
- You have purchased video/tv content on your Apple TV or other iOS device
- You want your podcasts sync'd across your devices
Why do you think it’s bad? I’ve heard others say the same but I’ve never heard a general (as opposed to esoteric) reason.
What won me over compared to Winamp was iTunes' smart playlists. I'm actually surprised they haven't borked, neutered, or removed that feature. It's still the same and it's still good.
It did a lot of other things right too. It was convenient to edit metadata for multiple files. CD ripping was painless and used a high quality mp3 encoder at a time when that was not a given. In general, it was one of those apps that just behaved logically to me and rarely if ever surprised me in a bad way.
When iTunes introduced "iTunes in the cloud" or whatever it was called -- the ability to have your files mirrored in the cloud -- I was more or less in heaven for a while. I had a few moans and niggles but nothing much.
I actively kind of hate it now though. Too many media types (with different paradigms) crammed into one app. The result is a mess. Not sure it could be any other way.
I haven't used it since. (Although it still starts automatically when I try to rip a CD using XLD.)
Now I use VLC for music on my phone and Vox on MacOS. Both are imperfect. FLAC isn't gapless in VLC, and Vox keeps trying to sell me things. But they work well enough to get some semblance of the job done.
The real problem is the conflict between utility and consumption. iTunes/Music were never there to conveniently manage and play audio (utility), but to lock users into a consumption silo. So importing and playing music from external sources has never been a design goal.
Vox has some similar issues, but isn't quite as bad. VLC is more of a utility app, which makes it more useful. (I suspect it has no problem playing an MP4 audio playlist.)
iTunes/Music has always been an unusual app, but there were work flows (play flows?) whose practicality has come and gone.
If you like listening to albums you can also keep them in your file system by artist, album, and song and have an easy time finding things.