Okay so this is what I want to happen:

When I update metadata in my library and I then sync with my iPod, I want not only the songs in the playlists that i've selected to be updated but also the information. My reason for this is I would like to have my iPod somewhat neat. My biggest thing is updated genre's and playlists so i have some comformity. I have figured out to sync just the playlists that I want, but it will not update the metadata. I know iTunes will do all of this...but lets be real I do not feel like completely re-organizing my library and something about iTunes just rubs me wrong. It could be the huge amount of space it takes up when it runs, it could be that you have to get quicktime as well when you download it, or it could be that it likes to take over your iPod.

Please let me know what you guys / gals have done as far as organization with your ipod? Have you resorted to iTunes? Or is it really not that bad? And did you reorganize your whole metatags so you could find things in iTunes like you had them in Winamp or the other player you use.

Thank you

~Tyler

I used winamp with my ipod a few times. Had to restore my ipod a few times as well. It got to the point where I sold my ipod because of it. Using you ipod with winamp or some other third party software is tricky. Most of the time your ipod will end up "forgetting" where the music is and say you have 0 songs yet it shows you are using 20 gigs of the hard disk. Check out ilounge.com, they have a few tut's to get it working without itunes.

i use a drag and drop program for mine, called yamipod....works like a charm, and you dont need itunes or anything to drag files to it, and you keep it in the ipod and you run it from the drive icon in My Computer

Thank you for input guys. What I ended up doing was relinquishing a lot of iTunes power over my iPod (like automatically syncing when I connect, and starting iTunes whenever I connect my iPod). What this allowed me to do was put videos, photos, and update my contacts and calendar using iTunes. While also allowing me to transfer music to my iPod using both iTunes or Winamp.

~Thanks again,
Tyler aka Twinscroll