Okay. I get annoyed by things in iTunes and think the whole application really is overdue for replacement -- I'd like to see things split up somewhat more like iOS, with a "Music" app, a "Video" app and (since this is the desktop) a device management app. But I confess that a lot of the lamentations about the UI design (not necessarily the UX design, which I'll circle back to in a moment) strike me as, well, highly overblown. I'm sorry the author couldn't figure out how to make songs repeat, for instance, but while the repeat icon has moved in newer versions of iTunes, it's literally the same icon as in the screenshot of iTunes 4 from a decade ago. (That's the earliest screenshot I could find.) And perhaps the Windows version of iTunes is uniquely horrible compared to the OS X, er, macOS version, but I can type the name of a song into search and have it instantly located; if I double-click a track name (or the big play arrow that shows up when I hover by it!) it just starts playing, but it certainly won't select a rating or a heart unless I click a star or a heart; so on and so forth.
I'd really argue the biggest problem with iTunes' UX stems from the way it's still, after all this time, inexplicably modal. I've never had a problem syncing an iOS device while it's playing music, as one commenter mentioned, but there are dialog boxes it brings up that are not only UI-blocking but process-blocking, which makes iTunes kind of a mess as a headless media server. (It still plays media, but won't be able to add any until the dialog box is dismissed.)
But I still cut iTunes a fair amount of slack. I've been using it for nearly as long as it's been available, I've subscribed to iTunes Match, I've subscribed to Apple Music, and I've ripped my own music library full of lossless tracks. Not only has Apple not, repeat, not, either deleted those or fiendishly replaced the files with AAC simulacra, it turns out to handle mixing my ripped tracks, purchased tracks, and "borrowed" tracks (i.e., ones that are only available in my library through the Apple Music subscription) pretty seamlessly. The introduction of Apple Music was a huge mess, admittedly, both in terms of UX and some teeth-grindingly poor song-matching algorithms (a distinct regression from iTunes Match on its own) -- but the server-side flubs seem to be straightened out now, and the current UI for Apple Music is pretty solid.
But, yes, I'm sure iTunes will be rewritten. I'm also positive that when it is, there will be a veritable explosion of thinkpieces that will almost all be variants of, "Who asked for all these horrible changes? iTunes was just fine! Apple is always fixing things that weren't broken! This would never have happened if Steve Jobs were still alive!"
I'd really argue the biggest problem with iTunes' UX stems from the way it's still, after all this time, inexplicably modal. I've never had a problem syncing an iOS device while it's playing music, as one commenter mentioned, but there are dialog boxes it brings up that are not only UI-blocking but process-blocking, which makes iTunes kind of a mess as a headless media server. (It still plays media, but won't be able to add any until the dialog box is dismissed.)
But I still cut iTunes a fair amount of slack. I've been using it for nearly as long as it's been available, I've subscribed to iTunes Match, I've subscribed to Apple Music, and I've ripped my own music library full of lossless tracks. Not only has Apple not, repeat, not, either deleted those or fiendishly replaced the files with AAC simulacra, it turns out to handle mixing my ripped tracks, purchased tracks, and "borrowed" tracks (i.e., ones that are only available in my library through the Apple Music subscription) pretty seamlessly. The introduction of Apple Music was a huge mess, admittedly, both in terms of UX and some teeth-grindingly poor song-matching algorithms (a distinct regression from iTunes Match on its own) -- but the server-side flubs seem to be straightened out now, and the current UI for Apple Music is pretty solid.
But, yes, I'm sure iTunes will be rewritten. I'm also positive that when it is, there will be a veritable explosion of thinkpieces that will almost all be variants of, "Who asked for all these horrible changes? iTunes was just fine! Apple is always fixing things that weren't broken! This would never have happened if Steve Jobs were still alive!"