Not sure if this is the right thread to post this in, but here goes: I am runnng PMW on a MacBook Pro with OS 10.10.1, and PMW 20.0.50. After much experimentation, I have the best luck by opening PMW first, then connecting the PONO player and selecting YES to "Load Music?"
The problem I am having now is that I sideloaded a playlist from iTunes (it actually copied all the songs, surprisingly) but they ended up scattered all over the place, since the playlist had 48 songs from about 20 different albums. As far as I know, there is no way to create a playlist directly on the player (correct? please tell me if I'm wrong about that) so I synced with PMW and created the playlist there.
I have tried two different ways to then incorporate the playlist onto the player: 1) drag-and-drop from the Playlists in PMW; and 2) syncing with Playlists selected. Both ways sent the software into an endless do-loop, where a progress bar opened up, but after 12 hours it still had acheived 0% progress.
Ideas, suggestions...?