Somewhere along the line, iOS device sync started working again.
Smart playlists still don’t sync correctly (they end up getting reshuffled when they end up on the phone), but I have a simple workaround:
- Have a smart playlist called Entropy Mobile with the shuffle rules I like
- Have a regular playlist called Entropy Queue, which is synchronized to the iPhone
- Occasionally copy the contents of Entropy Mobile into Entropy Queue
The nice thing about this is it’s also easier for me to curate stuff, like albums which got partially played, or where I want to move an album to happen later or whatever.
It’s still not perfect and there’s still some asinineness of smart playlists where they’re always incorrectly-shuffled when I first launch Music.app, but clearing out the list and letting it refill means it’ll be shuffled correctly. I guess the main downside is that I need to be a bit more deliberate about populating my phone with music, but that’s not necessarily a bad thing.