As a Windows user I don't like iTunes because it is an invasive, bloated, resource-hungry, and IMO poorly designed (UI) application. It is unintuitive to me, needlessly restrictive (par for the course for Apple in my experience), and generally crappy. I understand on a Mac, with more integration and with fewer great, free alternatives (like Winamp, AIM, MediaMonkey, etc.), it's probably the bee's knees, but on Windows the only reason I'd say anyone should ever consider it would be if they have an iPod. But I'd never recommend an iPod either for the same reasons as above (well, mainly the needless restriction and proprietaryness). And there are also better, free tools for managing iPod's on Windows. Anyway, I digress. I think pretty much all Apple software on Windows is crappy.
- Oshyan