[zerkten]

Lack of dogfooding is part of it, but I have to wonder how many product managers they've brought in to convert their player to a cloud music service?

Changes like requiring you to sync all your devices with Apple Music are part of many changes to try and make the transition. It's a big one because a player is very different from a service (historically something Apple have been bad at), but they've had a lot of time. Apple have been able to get this far because going "all in" is accepted by Apple customers more than those on other platforms.