I've been a WinAmp user since my first MP3 some three and a half years ago, and I've never had any kind of problem with it. It's done everything I've ever wanted. It's not flashy; it's just solid and functional, which is all I've ever looked for.
But I've been following the iTunes hullaballoo and, like a good trend whore, when the Windows version was released, I started thinking about trying it, which led, eventually, to...well, see the first sentence.
I don't do this without trepidation, however.
I don't like Apple products, on the whole. I certainly don't trust Steve Jobs any farther than I can throw him. There is too much of the grinning megalomaniac to him, to my eye (which is not an impression I draw from Bill Gates, for whatever reason; Larry Ellison is worse about it than Jobs, and Linus Torvalds just seems like a technified version of a damn dirty hippie). Some get bothered by perceived "bullying"; I, on the other hand, get frightened by charisma.
(Incidentally, I feel it necessary to point out here that the WinAmp download is approximately one-tenth the size of the iTunes download.)
Perhaps it's (yet another) personality thing. I'm an admitted control freak. Doing things "the easy way" (i.e., with the ease-of-use for which Apple has become famous) is often less important to me than doing things my way.
Anyway, I'm giving iTunes a shot (presuming this download ever finishes). I'll report back after a time of using it with whatever findings I may have.
I do not, at this point, think that I will be buying any songs from the iTunes store. I do not at all think that on my computer is how to listen to music.