This Oreilly.Net article entitled Hacking iPod and iTunes has some interesting hacks. I dont have an iPod, but i do use iTunes on my mac and pc (well, i use WM10 more on the PC, but i sometimes use iTunes) and some of the hacks are pretty cool. some really interesting things. i like the Apple Script hacks to get it to do stuff like rename songs in a given playlist. could be handy.