iTunes money pit
Found this post about a guy who ran up an tab from 8,000 downloads on iTunes (via Get Rich Slowly). That is one reason I consider iTunes to be evil. I had recently turned my wife onto iTunes and set her up on my account. Every time she made a purchase, it would email me the invoice the next day. I didn't really care what she was buying, since I figured a little here and there wouldn't hurt. And then, in the course of 3 days, she purchased 60 songs, and 40 in one day. In the emails, it lists the songs she bought, and skimming through it, I noticed a few of them were songs we already had on CD, or songs I had as regular MP3s.
At that point, I realized the problem with download services like iTunes. First, it is expensive to build up your library. We have eclectic music tastes, and what we feel like listening to at any particular time can vary greatly. I don't want to spend hundreds/thousands building up some music library. Second, you don't actually own the songs you buy. You basically fleece them. You can only use them on so many computers, with their software, etc. You don't own it. Third, it is too easy to get sucked into a buying fever. One click and you "purchased" a song. No swiping of the card or needing to go through some checkout process. It is too easy to buy more than you even realize.
The solution? Dump iTunes and get a service with a subscription. Apple doesn't believe in the subscription model, and so I'm not going to give Apple my money anymore. There are plenty of subscription music services from Napster, Rhapsody, Yahoo, and the one I'm using now, Urge (since it is right there in Windows Media Player 11). I can get all the music I want, when I want it, for a flat (and reasonable) rate. Why spend hundres/thousands building your library of stuff you don't actually own anyway, when you can just pay $10/month and get it all.
Typically I hate monthly services, though this is one time where I think it is justified.