Today afternoon I got something in the mail which I ordered nearly a month ago. It was an iPod classic which I ordered from eBay. I spent the entire evening organizing my behemoth music collection(which incidentally has four albums by the band behemoth). Here’s the breakdown and why I’ve sworn jihad against iTunes.
5:00 PM: I come back from lab and download and install itunes. I allow it to scan my music folder and it messes everything up completely. Turns out it only reads id3 tags, and some of my music wasn’t tagged properly. Winamp detected everything fine because of it’s excellent folder-tag detection service.
5:30 PM: I needed to tag around 49 gigabytes of mp3s and add album art soon. After searching around for nearly an hour, I found MediaMonkey. I discovered it had the amazing ability to search amazon for the album and download and tag everything and even add covers.
7:30 PM: I’m halfway through fixing my media collection. Now I have to go and play 5000 songs so the metadata is refreshed. I tried to clear the itunes library but I couldn’t. Finally I found the library xml file and deleted it and the library was emptied.
8:00 PM: I very carefully added only the folders which I’d freshly retagged and things worked a little better. All the artwork showed up in coverflow. I dragged all the music to the ipod and within a surprisingly small amount of time, everything seemed to work fine.
8:30 PM: I decided to see how the iPod works with winamp, because I’ve been using winamp as long as I’ve had a computer. It detected everything perfectly and even writing worked, and when I unplugged the ipod I realized that all the cover art was gone. The music was there but the cover art was gone. Now there’s no point with no cover art so I had to restore the ipod to factory settings before transfering everything again and I decided to wait before a more mature and stable version of the iPod management was coming to winamp.
9:00 PM: Tried loading in some video and TV Shows. Everything worked as it was supposed to except I seldom have the patience to watch a movie. I put Borat on the iPod hoping I’ll watch it on the flight back home. Also put a few family guy episodes for good measure.
Moral of the story: iPod rocks, iTunes sucks so bad, and winamp needs a bit more work.

Really ,tell me how you liked Borat after watchin the film :/
iTunes stores cover art in a seperate folder. Thus, the covers weren’t uploaded toyour ipod when using winamp. You might find a utility to transfer the external covers and embed them in your mp3 files (I know there’s a utility for max, but never searched for one on wintel or lunix).