Fighting my iPod ignorance

My gf and I bought eachother 60G video iPods for Christmas.

I am a lazy/sloppy digital music manager in recovery.

Over holiday vacation I ripped a handfull of my cds with iTunes while not online and without sitting at the computer and manually editing the ID3 tags appropriately. As such, I just transfered the numbered tracks to my iPod and then deleted them from my Library one cd at a time. Since then, I’ve been manually editing the ID3 tags of the files on my iPod.

Now I want to be able to get a copy of some of these files to my gf’s iPod, but I’ve run into the following obstacles:

[li]No dragging and dropping a selection of songs from my iPod to my Library[/li][li]The way the files are stored on the iPod make it tedious at best to find the specific songs I want my gf to have[/li][li]I left the cds I had ripped with my Mom so she could enjoy them until our next visit[/li][/ul]

Do I have any non-tedious options, or am I stuck in that grey area where what I’m trying to do is too indistinguishable from stealing music and therefor I’m screwed?

I can’t help you with the way the iPod sorts files - that’s just a function of how the firmware was written, and I don’t believe that it can be altered (or, if it can, that it would automatically change anything).

However, if you’re on a PC, you can use EphPod to get the files off your iPod. If you’re on a Mac, use iLinkPod. Once you re-import to your library, iTunes should read the ID3 tags and make life easy again.

Caveat: These are technically not Apple-sanctioned activities, just technically feasible.