Ah, got it. One of my greater fears is lost work (or lost time, which is basically the same thing), such as having to re-rip everything and re-tag everything if something happens to my iPod.
I made the decision long ago to always back up my iPod and got SharePod (freeware) to do just that. It "decodes" the filing encryption of your iPod and copies the contents, or just selected songs/albums/genres, to your hard drive. Everything copies, including album art and all tags, and you can organize the results any way you want. In my case, that's folder levels for genres, artists, albums, and songs within the folder. Folder name for the album includes year of release as a "prefix" (so they appear in chronological order), and filenames for songs include track number.
If that sounds like a lot of work, it's not. It takes two minutes to set up the application, then every time I put new tunes on my iPod, I back them up and everything is done automatically. I can now remove songs, albums, artists, or entire genres from my iPod, or load them back on just as easily, and again, all tags and album art are preserved.
Someday, I'll have some other mp3 player and I'll drag and drop to load/unload tunes. That'll be nice. But even then, having everything organized is the key. Yeah, I'm pretty anal, but the amount of time saved has already far outweighed the initial investment in setup time, by several hundredfold I'm sure. And this is music we're talking about.