Forget iTunes use Winamp to sync your iPod
If you are like me you have an iPod and have downloaded iTunes, but you prefer to manage your music collection through either Windows Media Player or Winamp. The thougt of recreating the wheel in iTunes is not too appealing, Thank goodness the latest versions of Winamp (not sure when it happened extacly) allow you to sync your iPod. That means you can browse to an existing playlist, add it to Winamp and then send it to your iPod. Winamp even creates the playlist on your iPod too!
More from Winamp.com:
Sync Your iPod® (or other portable player) with WinampYou love Winamp and have an iPod® and don’t think they will work together? Think again. Winamp 5.5 includes iPod® syncing support with album art view. To synch Winamp and your iPod® (or other portable media player) launch the Media Library and check out the ‘Portables’ tab. You should see your iPod® or other device (provided you’ve plugged it into your computer!)