Unfortunately, I’m not that sort of person, either, but I see that WinAmp gets recommended a lot for Windows users. If you’re a Mac or Linux user, I don’t know.
On a vaguely related ramble: My consumer media interaction is pretty much limited “store it, burn it, stream it, sort it, let me make playlists out of it, and get it onto my devices,” for which iTunes is more than adequate.
Usually the signs that you’re not going to like iTunes are (a) when you spend a lot of time with metadata (iTunes batch editing is a bit clumsy, and it can’t easily be scripted unless you know Applescript on the Mac), (b)want to arrange the physical media files yourself (iTunes HATES that–you will break the library doing it), (c)have a device that doesn’t interact with it (i.e. you have to manually drag and drop stuff, which is sort of a special case of (b)), or (d) trying to have the device (rather than the iTunes library) be the definitive source of media.
Almost everybody who personally comes to me for help with iTunes doing “weird stuff” are geek types who have been doing (b): “I moved the music folder, and it doesn’t work!” “I deleted everything that wasn’t a media file and it doesn’t work!” “I rearranged the music into folders the way I like and it doesn’t work!” “I deleted the entire iTunes music folder, and it cleared my device when I synced! Why did it make me lose all my music!” “I drag-and-dropped a bunch of music from my device into the music folder and it doesn’t work”
If you like doing that stuff, best to either keep two copies of everything, or skip using iTunes altogether. iTunes is meant for that 80-90% of the population that just want stuff to work, and doesn’t care about the implementation. There’s nothing wrong with not being in that population–what gets folks in trouble is being in the “needs more control” camp and trying to use iTunes anyway.
(d) is the dreaded “I got a new computer, and didn’t bother to copy the library from the old one, since my music is on my iPod” syndrome. iTunes can handle that case, but only for music from the store or iTunes match (i.e. music for which is knows for sure you’ve got a license). Protect (back up and maintain) your iTunes libraries, folks! (This applies only to folks who sync with a computer, which is no longer required as of iOS 5 (6?). If your iOS device does it’s backups/music transactions only from the cloud, and you never sync it with a computer, you won’t have any “unknown origin” music on it, anyway, and you can get it all back from anywhere.)