iTunes started out as a mediocre Music app, and got worse year after year until the shit show of Music. 💩🎶
~ Aristotle Sabouni
When Apple came out with iTunes in 2001, it wasn't horrible. There were better CD rippers (copying CDs to Digital Media / MP3's), better Music Library Managers, better media players, and better disc burning software -- but it did all of it in once, did it failed well (for superficial use), and came with the machine.
The thing it did poorly, is music management -- old Apple would have put in the time so that you could both manage your music in their hierarchy, or use your own (just point to a root folder, and it would figure it out). New Apple (NeXT) just did things like copy assets to where it thought they should be, leaving multiple versions around, and just being dicks. If you were a casual user, it worked well enough. If you liked having control over your assets/organization, it was a steaming pile of crap. And it didn't need to be. But it was.
Then they kept adding functionality and making it worse; designed by a committee of bean counters and featuritis, without fixing any of the underlying issues.
- They changed the music format to their own proprietary AAC -- with no real value other than incompatibility with other devices. Fuck you, I won't buy your music knowing I can't use it anywhere else.
- They added lots of hardware support for iPods, later iPhones/iPads and so on -- all without the ability to browse/sync/manage the device when it wasn't connected.
- They kept adding features in ways that made it very modal and unpredictable, especially across versions. And things like smart playlists versus my own, iTunesDJ (later Genius) so they could feed me shit they wanted instead of letting me control my playlists.
- HomeSharing that only half assed works.
- Synching across devices that almost works reliably.
And then, worst of all -- they broke the cardinal rule of software. Never shit on the customers data.
During one of the transitions (like to Apple Music), it decided that all of the music I'd ripped, didn't need to be copied on an upgrade of laptop->to->laptop. It just didn't copy it out without warning -- and by the time I recognized it was missing, it was gone.
The phone still had the music -- just my master library was gone. And of course to prove they are AppleHoles, they wouldn't let me download my own music from the phone to the laptop to restore the database. So I had to get a 3rd party App, that defeated Apple security and let me download my music to my desktop. And of course that failed, because Apple couldn't resolve the new arrangment for the music and their database. So I had to rebuild my Library, which lost all my ratings, playlists, and so on.
I will never trust a company that will destroy my data without my permission. (Even intentionally omitting migrating it). Never, ever trust Apple software. Pages / AppleWorks, and a dozen other of their apps have done this to me. Where they upgrade a version or two, and break backwards compatibility. They might have a single version migration -- but after a couple of versions you can have old files that are orphaned and unopanable. So iTunes/Music is casually usable -- and fundamentally poorly designed software.