Rockbox

Okay, here’s the idea:

Right now it’s easy for a user to accidentally clear his settings by plugging the iPod in with Hold enabled. I feel that this shouldn’t happen.

Firstly: If the iPod is already in Rockbox, Hold should prevent the reboot. This allows for easier charging during playback (it can be hard to hold the menu button down while plugging in a cable, sometimes, at least if you’re trying to plug in the dock connector end to an iPod that has a case on it). This also prevents accidentally booting to disk mode with hold on (which prevents accidentally leaving disk mode with hold on.)

Secondly: If you insert the USB cable to wake the iPod, with hold on, it should (in my opinion) enter Rockbox instead of Disk Mode. This would then allow auto-resume and car mode to work fairly well I think (the iPod would only need to shut down automatically when power is removed, and everything else would be handled by existing functionality). Then to use car mode a user would simply have to set it, set their volume, start playback with resume on startup enabled, and flip hold on.