i sold my iPod (along with the RAZR and Nokia 770 whose collective functionality the iPhone supplanted -- yay for convoluted sentences).
about the startup volume deal: i have my iTunes library on an external drive. Audioscrobbler only looks at iTunes libraries that are within /Users/username/Music/iTunes Music Library or whatever the actual path is.
My iPod never gets detected by Last.fm.
[...] Also note, iPhones are NOT supported.
My iPod is detected but no tracks get scrobbled.
Have you set your iTunes library to a custom location? If so, Last.fm might not be able to find it. We will add an option for specifying this manually in an upcoming version.
Funny, I keep all of my music on a partition of my hard drive and have no issues submitting tracks to last.fm - not to mention all my iPod tracks usually get synced as well. At least, I think they are?
EDIT: I don't really tag a lot of music though, I wonder if that affects my OMI or not? Interesting. I don't get out there on last.fm that much, but whenever I do I always think I should use it more.