I think it's a combination of both scale and people's expectations.

As the size of your music library goes up, the UX changes. The original iPod UX was (at least for me) genuinely awesome. It became less awesome as iPods got 40, 60, and larger storage, and it was pretty much unusable when I modded one to have 1TB of storage.

And related but different, everybody's expectation of what "a large music collection" is varies wildly.

I don't necessarily think this is intentional enshittification, I lean more towards "there's no right solution for everybody, and there's probably not even a dozen different right solutions that encompass most people".