You know me: I used to be anti-iPod and anti-iTunes. I ripped my music with 3rd-party software and had a iRiver 40 GB MP3 player for about two years. After a while it was frustrating to manage my music manually and have to remember where I put things. And when the iRiver started to go south on me, there wasn't any tech support out there to help me, nor was there a clear upgrade path to a new iRiver MP3 player (they had phased out their big hard-drive-based players by 2006). So I bought an iPod. Yes, iTunes is a resource hog and doesn't always play well with Windows. No, iPods don't play protected WMA files. But you know what iPods do? They play MP3s, and they play them well. I'm on my 2nd iPod and I love it. I wouldn't go back to another player now. Before you buy something else, try one at an Apple store or check out a friend's.
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Welcome to the 21st century, BTW.