iPod Folder Tree

You are thinking wrong if you want to work at the Finder level to organize music. Stay out of the Finder (or Windows Explorer) level with iTunes (and iPhoto too)! Organize iTunes music ONLY within iTunes. If you mess around with files at the Finder level you WILL eventually corrupt something. And it WILL be bad.

If you have free time today do a search on 'Smart Playlists' both here and at the Apple Support website - that is the direction you should be looking.

I'll try to help with another post this evening when I'm off work.

 

There are others that frequent this forum that are MUCH more knowledgeable about the inner workings of iTunes than I am.

You can set iTunes to allow you to manually manage your music - Preferences > Advanced > uncheck 'Keep iTunes Music folder organized.' I'm not sure if that will satisfy your requirement though. I have never tried that because I don't care how iTunes organizes at the file level. All care about is that I can find the song, or artist or album I want relatively fast. And I have accomplished this by setting up my Smart Playlists.

I did find this discussion thread that might give you some ideas of accomplishing your requirement:

http://forums.macrumors.com/showthread.php?t=413810

I do know that it is very important to only work iTunes files from within iTunes.

Sorry to keep you hanging all day for what is a pretty weak reply to your question.