Well, cute little pinkness and nice hardware aside, I was really unhappy with my Zune because I hated the Zune software, I was definitely not going to use it as my main media player on my computer, and even with hours of hacking it with the ZAlternator, I still couldn't sync playlists on to my Zune with WMP, which is what I normally use for all of my music listening.
So I returned it, and now I'm looking for a replacement. I have done some looking into iTunes, which seems to have all sorts of problems that I am not really excited about--after all, that would be a whole switch to a new media player and I want to like the software that I have to use. But maybe WMP is equally annoying and I'm just used to it.
I want to be able to organize my music how I want to, rate it how I want to, have playlists and sync those to whatever device I end up with, and be able to listen to music easily. I am really concerned about files being changed and unable to be used on another computer (ex--when I upgrade someday from my 2005 Gateway laptop) with iTunes, although I know that there are similar protected rights associated with Windows-purchased music.
Does anyone have any advice or insights to share? I want something not terribly complicated, and I want to be reasonably satisfied with iTunes if I do switch from WMP. Apple seems to do music right (unlike Microsoft, who made a product that doesn't work with OTHER Microsoft software), but I don't want to think that and have another Zune disaster.