Honestly, years of using iTunes daily on Windows completely turned me off of the idea of switching to a Mac or an iPhone. Without exaggeration, it is one of the worst pieces of software I've used. It's bad enough that my next MP3 player probably won't be an iPod, despite generally being happy with the one I have.
Edit: and so this isn't just me ranting about iTunes (yet again, sorry), I think iTunes can actually harm Apple's image. It's tolerable if that's all you've used, but when compared to pretty much any other music player, it has glaring flaws (at least on Windows). To make a terrible continuation of the analogy, a Trojan Horse doesn't work if the Trojans hate your crappy horse and decide to never speak to you again.
Interestingly, when it first came on the scene as SoundJam, and in its earlier incarnations at Apple after it was bought, iTunes was by far the best music player out there[1]. The overwhelming favorite MP3 player on Windows at the time was WinAmp, whose UI was a ghastly collection of inscrutable, tiny fonted palettes. Compared to that, having your entire collection of music in a smart, scriptable database with a slick interface was a dream.
Performance problems on Windows and tacking on one new non-music playing feature after another seems to have doomed the experience and reputation.
Edit: and so this isn't just me ranting about iTunes (yet again, sorry), I think iTunes can actually harm Apple's image. It's tolerable if that's all you've used, but when compared to pretty much any other music player, it has glaring flaws (at least on Windows). To make a terrible continuation of the analogy, a Trojan Horse doesn't work if the Trojans hate your crappy horse and decide to never speak to you again.