Q: I use the Apple wired remote with my 4G iPod so I don’t have to take my iPod out of my bag when I’m on the train or walking. When my playlist or album has ended, pressing Play on the remote starts playing my whole library from the beginning. Is there anyway of changing it so that hitting play will shuffle the songs instead?
A: Unfortunately, no.
After you finish a playlist or an album, the iPod reverts to its default location, which is at the very first song (alphabetically) in your library. Even if you change the main menu display, pressing the Play button on the remote still starts from the first song.
What you could do is turn on shuffle on the iPod (Settings > Shuffle > Songs), which will shuffle everything by song, including albums and playlists.
It’s not the ideal solution, since it will prevent you from listening to an album or playlist in order, but it will let you shuffle your songs after the end of an album or playlist.