I like iTunes a lot. I've been a WinAmp fan since the beginning, and it took me a long time to accpt iTunes. I thought iTunes was too big on the screen and took up too much memory. I liked that I could get WinAmp down to a minimal space and memory footprint. What did it for me was that iTunes approaches your library as music, while WinAmp approaches it as files.
You have to really look hard to see a file name in iTunes. It treats every files as a song and gives you that information in a well laid out and organized fashion (something WinAmp lacked for a very long time). WinAmp always seemed to be at the mercy of people's poor file labeling and id3 tagging. When I stick in a CD to iTunes, it will rip and file it away without me having to tell it where to put it or how to file it. It starts paying the songs as I rip. Same sort of reverse funcationality with burning. It just works, and it works in a way that I appreciate and my sister can still understand. WinAmp just no longer does it for me. While I still appreciate it's simplicity, it just seems like it lacks refinement. It's great for playing files, but it doesn't do it for me when it comes to overal library management.
And don't get me started on the clusterfuck that is Media Player. If any of you use Media Player to manage your library, you deserve for your computer to catch fire.