It was just a matter of time.
For the first time ever, I actually bought something on iTunes because of collaborative filtering (for the record, it was "Emerge," by Fischerspooner).
In my brief time using iTunes, it has frustrated me on many different levels. I am a frequent Amazon.com user, and I've gotten used to their level of personalization and collaborative filtering. They say "We thought you might be interested in..." and they might as well have said "Put this in your shopping cart, now!" I'm used to them reminding me that I looked at Grey's Anatomy on DVD the other day and saying, "oh, crap, I was going to buy Grey's Anatomy on DVD!" That sort of thing.
iTunes is not nearly so helpful. If you were, say, listening to previews of some of the songs on the 97x Top 97 list one day, and came back the next deciding you were going to buy some, well, you're on your own finding that list again, sucker. Because search won't work and iTunes isn't going to HELP YOU SPEND MONEY by indicating what you looked at recently. They do provide other top downloads and related artists and other such stuff, but I still feel lost half the time on iTunes. And they don't have that uncanny knack for constantly knowing what you want even before you do.
And don't even get me started on the usability issues. The search text box with no button! Argh! Sure, it's all Appley streamlined and sleek, but there's plenty of space for a search button that would keep bunches of users from getting tripped up (myself included).
I've got similar bones with the iPod, although I like mine. Such as having to reformat the damn thing to get songs off. They call it synching your iPod, when you hook it up to the computer so it can have its little mind meld with iTunes. But it's not SYNCHING if it doesn't remove from the iPod the songs you've removed from iTunes. What it's doing would be better termed DUMPING. It's a good thing PDAs don't synch with Outlook this way or executives around the world would be showing up for cancelled meetings all the time.
And then there's the scroll wheel, which I use daily to blow right past whatever artist or song I'm trying to find. I thought that I would get used to it, but I think operating something primarily with your thumb might just be inherently bad ergonomics. Someone posted this critique of the iPod on a mailing list I'm on, and I found myself nodding my head to the whole thing.
But I'm going to keep the iPod for quite awhile, because it is still a hell of a lot better than my ginormous MP3/CD player, my previous mobile music solution. And I'm stuck with iTunes until somebody else comes along with something better. Come on, Amazon, you know you want to!