Syncing to shuffle from a big playlist - updating/switching songs
I have a small iPod shuffle that I use for the gym. I have a lengthy gym playlist on iTunes (much bigger than the capacity of my shuffle). Historically, when I'd get to the end of a 'cycle' of songs on the shuffle, I'd plug the shuffle into my computer and ask it to resync with the playlist - it then picked a new bunch of songs at random off the playlist, so I got different tracks to listen to (obviously there were always some that 'stayed' because of the nature of randomness, but a sizeable chunk would come off the shuffle and be replaced with different songs from the playlist).
However, since upgrading iTunes it looks like I can't do this anymore. There is no option to ask my shuffle to sync with the 'gym' playlist at random - it simply copies the first x number of songs over in alphabetical order. Is there a way to sync it with random songs off the playlist like I used to? This is very frustrating!
OBS,iPod shuffle (2nd generation, Late 2008)
