My 80gb iPod is close to full and I will almost certainly use it as my music source in the car (with or without a Y cable as needed!?).
However, I am intrigued by the possibility of using a flash drive. My novice concerns are that:
1. Album/playlist track orders are not correct.
2. I don't know how to tag tracks as also being in a separate playlist (I'm fairly sure you can't and that instead you would have to save repeated copies of tracks in their respective album and playlist folders).
3. I have no idea how to get the album artwork out of iTunes and tagged to the tracks on my flash drive.
I'd still like to keep my options open though, so if anyone can direct me to a helpful guide or resource on the best way to go about this, I'd be really grateful.