I add songs to a Playlist and then randomize (physically) the order before syncing to my iPhone and Nano. I no longer see a way to do this in 11.
Before asking why not use Shuffle on the iPhone...here is what I do.
1) Have a large Playlist with the music for my device(s) sorted by date played (almost all ALAC).
2) Copy 250 of the oldest last played songs to a Playlist named Random and then randomize them so they dont play in the same order as last time.
3) Copy to another Playlist named iPhone so I can fine tune (like moving same artist that are one after the other and...) then sync to my iPhone and play in that order.
Before asking why not use Shuffle on the iPhone...here is what I do.
1) Have a large Playlist with the music for my device(s) sorted by date played (almost all ALAC).
2) Copy 250 of the oldest last played songs to a Playlist named Random and then randomize them so they dont play in the same order as last time.
3) Copy to another Playlist named iPhone so I can fine tune (like moving same artist that are one after the other and...) then sync to my iPhone and play in that order.