I feel like in the GNOME world, it's often an unspoken assumption that Apple sets the standard for good design, and that the free software folks just hobble along trying to meet it.
Having not used Macs extensively since the quite-well-designed OS 8.6, I've often assumed this is true (nevermind the poor design of the "Dock" etc).
With K's lovely new iPhone, I had occasion to download iTunes lately (and I kept Windows on a partition of my new laptop just for this purpose -- ugh). This is a sort of submission, ever since my unfortunate altercation with a Mac Genius last time we bought a Mac product, when said genius knew virtually nothing of what file formats the iPod supported and could only tell me, repeatedly, "you just use iTunes."
Well, now that we have an iPhone, it appears you in fact have to use iTunes (things don't just work in Ubuntu with it, and you can't buy cool stuff for it without iTunes anyway), and all I can say is iTunes deeply, deeply suck.
Here are just a few experiences so far:
1. I try to copy a movie to the iPhone. I drag and drop it -- this is the paradigm of virtually every mac app everywhere since multifinder was introduced. This starts playing the movie. Nowhere can I figure out how to exit the movie -- I finally quit the program and reopen, at which time I have to reenter my password information.
2. I can see my shared library from my Rhythmbox machine -- sweet! But I can't copy the songs or download them to iTunes, even though they're DRM-free easily-copiable songs in the linux world (I only buy music from Amazon so as to avoid DRM).
3. I copy my music library into iTunes from a networked folder since the "magic" way didn't work and the app hangs. I have to force quit the application, leaving me with about 1/5 of my music library.
4. I try to "sync" the iPhone to the program in order to let Katharine update her Audobon app and install her newly downloaded TV show. I get a series of confusing messages about syncing "erasing" everything on the machine. Finally, I click "OK", rather frightened of Katharine's losing all the apps she's already paid for. Fingers crossede.
Long story short: the "syncing" model is rather confusing, iTunes is buggy and doesn't seem to be threaded properly so that one operation (importing a library) hangs up the program with no easy way to pause that operation. Furthermore, long operations such as syncing don't include time estimates.
Of course, on the plus side, the iPhone itself is pretty sweet. According to K anyway -- I don't really get to play with it much, and I don't dare to since I might want to write apps for it, which dooes not exactly promise to be a free and open experience to say the least.
I'm pretty sure any neutral comparison of iTunes to Rhythmbox would have Rhythmbox dominating iTunes in usability and feature set. Except, of course, the ability to work with the Apple store -- but that's not exactly Rhythmbox's fault.