Apple views themselves as a hardware company and they'll give away software if it boosts hardware sales. iTunes is an obvious example. I could definitely imagine a scenario where Apple makes MobileMe free for iPhone users.
I hate iTunes. Even when I'm using my wife's Mac. It makes everything I want to do difficult. Seriously, Apple needs to learn from Valve and Steam.
Recently I picked up an Apple TV. My wife was having problems ripping movies for the kids (much safer than letting the DVDs get trashed) and then getting them to run through the media centers on one of the consoles. So, I went and got an Apple TV.
Apple TV is mostly nice, but it has it's warts. First, the syncing is horrid. I have issues syncing while Apple TV plays movies. It can't, or at least, I can't find a way to do it. So, if someone is watching something, and it needs to Sync, NOOOOO. I've had this problem with my iPod, with Sync being the harbinger of death.
Anyways. The next issue is movie files that disappear. I've synced videos, played those videos, and then the videos have disappeared, or just stopped working. Or iTunes will tell me it's synced, and it won't show up on the Apple TV.
Seriously, Apple, Google, Microsoft, and others really need to start working together. The Internet works far better than any crap they've put out. Grrr... frustration, nerd rage!!!!
I love iTunes. It has all my music in a scriptable database with a wonderfully configurable front end. I've never understood the hostility that's developed over it, other than possibly sour grapes Windows users forced to use it because of their iPods. Before iTunes, I used WinAmp, which was garbage. Maybe there are better programs now, although I can't imagine what else I'd want to do that iTunes doesn't make easy for me.
It all comes down to different ways of doing things. Some people like to manage their music more manually, copying over mp3 files to a folder. I am in this category, because I like complete control, and some of the things itunes does seems to be confusing. Also, I don't see the need of having mp3 files on a hdd, then stores on my iphone, then also stored in the itunes music folder. I don't need 3 copies of a music file. This is one part that frustrates me. Another frustration was silence between tracks, which itunes did not used to support.
However, I completely understand why most poeple like itunes, because most people aren't like this, and itunes provides a very simple interface for them to do it.
Saying that, the Windows version of itunes has not been as good as the mac version. And even on the mac, it seems to pause when copying over lots of large mp3 tracks, although this has gotten a lot better in the recent release.
iTunes is a poor media manager, mostly because it's focused on become a DRM System. Just think about what it really does, what it really syncs. iTunes handles applications, of all things. If you remain with Apple's ecosystem, everything will be fine. Go outside that, and everything starts to break down.
I used to be a Mac user and always hated iTunes. It always felt like it was fighting me and trying to force me to do things its way rather than my way. Asking it, for example, to play music stored on a remote samba share tended to make it copy the music to my hard drive rather than, you know, play the music.