C:\Users\Music\Festering Maggot Jackhammer\Apashe_x_cherry_lena_feeling_good.mp3
Is the reason they don't play because the location of the file is wrong? How to fix this? Won't windows potentially assign the ipod a different drive letter each time its connected?
Rockbox will treat the drive letter as being the disk your iPod is on, so its looking for this file on your iPod:
\Users\Music\Festering Maggot Jackhammer\Apashe_x_cherry_lena_feeling_good.mp3
You could find and replace that path to where your music really is, put your music in that folder on your iPod, or use some other tool for making playlists.