Using iPod as primary storage for all music, help!

Hello all!
Okay, so I bought a 60Gb 5G iPod last month and I'm loving it. However, I'm using it a little differently than most and because of this I'm unable to use many of the conventinal "cures" people have suggested. Here's my situation.
Rather than having my music stored on my computer and then syncing with my iPod I actually store all of my music on my iPod so I can take it back and forth to work with me and play all of my music on my work computer and my home computer. Everything has been going just fine but I've run into a problem with album artwork and the traditional fixes aren't an option.
The problem is that artwork that I've added directly to the iPod isn't showing up on the iPod when I play it when it isn't attached to a computer. I know this is because artwork needs to be added to iTunes and THEN transferred to the iPod.
So, how does someone like myself who isn't managing through music on their computer's hard drive go about correcting such a problem? I don't want to dump everything off of the iPod and back onto my computer, just takes way too long. Can this problem be solved by accessing the iPod DIRECTLY through iTunes?
Thanks!
5G iPod Video   Mac OS X (10.4.2)  

You're welcome.
Although you haven't seen many reports of iPod hard drive failure, it can and does occur as it can with any hard drive.
Maintaining a regular backup of all important data is very important if not the most important. It isn't a matter of if but when a hard drive has a partial or complete failure since none last forever.
I learned this painful lesson the hard way. Without warning, I experienced a complete hard drive failure on a G3 PowerBook less than one year old and the only time I've experienced this but it only takes once. Apple replaced the hard drive under the standard 1-yr warranty period but none of the existing data was recoverable. I didn't maintain a backup at the time and I lost everything.
Currently I use a 3rd party backup utility called SuperDuper! which creates a complete bootable clone backup of my hard drive saved to a Firewire drive. It includes a Smart Update feature which updates files that have changed only between backups.
I never want to go thru that painful experience again so I emphasize maintaining a backup when I see an opportunity to do so. Always better to be safe than sorry.

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