iTunes used to be a great program. A single place to both organize your music and do your music shopping (i'm old enough to remember when being able to buy any song as a $.99 single was transformative), it served its need and served it well. However, as time has passed it's become a hopelessly bloated, unusable mess. A function of trying to do too many things, it's lost the simplicity of the best Apple products. There are many things to complain about (why force installation of Quick Time with iTunes? Why shove Genius down our throats? I don't want you do download my "safe browsing data"! etc.) Today, however, I'm going to focus on a small thing: album covers.
It's no secret that i'm a music geek. I love learning everything about the songs that I listen to, and I enjoy having an album cover with my music. In fact, one of the things I loved about the iPhone was that you could easily display the album cover for all of your music. One right-click later and voilà: there was your cover! But somewhere along the way, iTunes got confused. Now when you download an album cover, it's frequently only for one song, not for the entire album. Or the cover is attached to the album, not the song, so it doesn't port over to your iPhone. Why not? I can see it in iTunes and i've "synched" the two devices! Are these not two apple products? Makes me wonder what else isn't being synched. And in perhaps the most frustrating part of all, you can't directly copy album covers onto your iPhone! You need to download the album cover, make sure that it's attached individually to every song on an album, and then you need to reimport your songs to your iPhone! And even that's not guaranteed to work! The end result: I have perhaps half of my music collection that displays that annoying "generic album cover" on my iPhone with no easy way for me to remedy the situation.
If you buy your music through the Apple Store, then you'll have none of these problems. And I suspect that that's the real culprit behind iTunes disintegrating utility: their focus on pushing you to buy stuff through them to the exclusion of supporting all of the other ways you can get music (download from other sides, burning music from actual CDs, etc.)
In my next rant, i'll go off on how poorly the UX is in both iTunes and the iPhone with podcasts. Until then, feel free to use my soapbox - i'll leave it right here for you in the comments.