I have a 30GB 5g iPod Video. Since the iOS is (was?) a total piece of shit, I swapped it with Rockbox. It's the most convenient thing ever. I can play almost any music file type. I can make dynamic play lists, by selecting a song and simply holding the middle button, then inserting it in. I can easily listen to an album. My songs are arranged according to the folders I put them in. And no iTunes. Plus, I can show off to my friends by playing Doom on my iPod.
I rue the day it breaks down. Apparently Rockbox doesn't work on newer iPods. So I'm keeping an eye on this thread, too.