I installed RockBox on my iPod this afternoon. RockBox is an alternative operating system for iPod and several other MP3 players.
I really liked it. It had theme support and you could customize the interface. It appeared that it does not change file names (I assume it would solve the song duplication issues). It uses standard .m3u playlists. What wasn't to like?
I was happy with it and ready to start discovering its full potential until I dropped my iPod onto the connector on my clock/radio. The clock reset itself. It's a self-setting clock so it wasn't a big deal but bothersome. I made a quick settings change that I had seen earlier and that fixed that.
I picked up the remote, turned on the radio, set it to iPod mode, pressed play, and... nothing happened. I had wondered about this because if you pause playback and the player goes to sleep and ends up back at the main menu, you have to select 'resume playback' from the menu. You can't just hit play and have it pick up where it left off. Which means that if I ever wanted to set the alarm to start up the iPod, it probably wouldn't work.
Sorry, RockBox, you had to go. :(