There’s over 2,000 songs in my anime and jpop playlist that I want to hear but my iPod keeps playing the same songs over and over. The Shuffle feature doesn’t seem to help either. I’ve played around with the Last Played feature and achieved the desired results.
Create a Smart Playlist with the Last Played and “is not in the last” option. Go back in time as far as possible then stop where there is still music. This is your first playlist. It may only have a few songs–songs you haven’t heard in the longest time. Your first few playlists will be sparse. Keep adjusting the time forward to keep songs in your playlist. The drawback to this playlist is having to adjust it.