I'm currently letting iTunes manage my music, which is something I've never trusted it to do.
I have about 8GB of music that's only on iTunes music folder and everytime I rip new CDs or download new songs I just put them in my Music folder, which I have added to my iTunes library - without copying it.
iTunes has already arranged that batch of 8GB of music into artist folders but I'm not letting it do the same with the new music I put on the Music folder. It's a bit of a nightmare, the music is all over the place and instead of being organised it's a mess. To top it all, the file names are sometimes wrong. For example, I ripped Amy Winehouse's Black to Black and the song name comes up as Amy Winehouse - Tears dry on their own, for example. So instead of the tag being Name of song: Tears dry on their own and Artist name: Amy Winehouse, it's all down as filename and name of song. Then in my iphone, when I wanna listen to the music, it's impossible to find.
On PC I used to use Media Monkey for this. I don't know what to do know to change all the file names and correct them. Help somebody!!