I had made a smart play list that chose one hour of music at random, to make my hikes a little more interesting. This way, I don’t have to check a watch. I never could figure out how to get iTunes to choose a new set of songs though.
I figured it out by accident tonight. Select the songs in the playlist and press delete. It will delete the songs and then fill the playlist again.
This is not intuitive to me because as an engineer, I see an auto playlist as something that is mutable. You should not be able to edit the list (the computer created it after all!) so I never tried. Bad UI, but I guess we learn how to work around kludgy UI all of the time.
I feel, so, Windows like…
P.S. I would have preferred a “Randomize again” or “rebuild playlist” option in the playlist’s contextual menu.