I'm posting this in music because that's what it mainly deals with but it works for video and other stuff too...
Winamp can work with your Ipod and that's liberating!!! I've been using this technique for a while now since I have big issues with iTunes and Apple specifically for choke holding their clients.
I've found this tutorial for those of you not so technologically savvy 
Hope this will you give you the courage to get rid of that crappy app and convert to WinAmp for your musical needs :D