I have to agree thatiTunes is pretty annoying, as was one of they key reasons I stayed away from using iPods personally, preffering players from Archos, etc.
However on getting my iPhone, itunes has become somewhat of a necessary evil, as I need it to Sync content onto it. With the comparatively limited 16Gb space I have on it, I have to do it pretty regularly, as Once I add in apps, photos, etc, Very little space is left for music.
One of my pet peeves is that while the iPhone will let you download podcasts directly on the device, it will not actually delete them. Deleting them on the device, just removes the listing but doesn't free up any space

. You have to sync to do that.
What I have to say is that after switching to a Macbook Pro a few weeks ago, iTunes has been much more stable on OSX the it ever was on windows.