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.