With the introduction of Apple Music, Apple confusingly introduced a
confusing service backed by the iTunes Store that’s confusingly
integrated into iTunes and the iOS Music app (don’t even get me
started on that) and partially, maybe, mostly replaces the also very
confusing and historically unreliable iTunes Match.
So iTunes is a toxic hellstew of technical cruft and a toxic hellstew
of UI design, in the middle of a transition between two partly
redundant cloud services, both of which are confusing and vague to
most people about which songs of theirs are in the cloud, which are
safe to delete, and which ones they actually have.
Even Jim’s follow-up piece, after meeting privately with Apple in
PR-damage-control mode, is confusing at best about what actually might
have happened, which is completely understandable because it sounds
like even Apple isn’t sure.
I have plenty of plausible theories on why iTunes didn’t get the
iCloud Photos treatment — why Apple Music was bolted onto this
ancient, crufty, legacy app instead of discontinuing iTunes, dropping
its obsolete functions, and starting fresh with a new app and a
CloudKit-based service. (Engineering resources, time to market, iPods,
Windows, and people with slow internet connections.)