I can’t figure out iTunes.  It’s supposed to be the center of Apple’s digital media universe, but I find it impossible to use.  I’d rather not use it at all, but I have an iPhone which I love and my wife has an iPad which my kids love and both require me to hook up to iTunes for some reason.  We don’t have any music at all on either device, but we still have to use iTunes.  Also, there’s an app on my iPhone which is called iTunes but it refers to the music store; I just figured this out.  There’s a separate app, called iPod, for playing music.  Incomprehensible.

I have a music collection, mostly ripped from CDs but also bought from the iTunes store or — more often these days — from Amazon’s store.  Apple’s DRM also doesn’t make any sense to me; I’m always having to authorize machines and log in with my password to get at *songs I purchased from Apple.*  In practice, it’s much easier to buy DRM-free music and do what I want with it.  Which means, for me, music arranged by artist in folders on Dropbox, sync’d to whatever machine I happen to be using; Ubuntu, Windows 7, Mac, whatever.  (Playlists remain a maddening problem; there’s a little business there.)

But I figured I’d put some music onto my iPhone; my only option is to use iTunes.  So I tried to introduce iTunes to my Dropbox music collection, but it choked on the 12 gigs.  So I manually selected bits of it at a time but I ended up with a bunch of duplicates.  These are all still files living in the same folder, but iTunes thinks that I have multiple copies of what it recognizes as the same song; for example, Ina Kamoze’s “Jump for Jah.”  The metadata is identical; the underlying file is identical.  But I only want one in my music library (why the library isn’t a list of files is baffling to me, but this is apparently common; a lot of image libraries work the same way).  So I ask iTunes to find duplicates and delete one copy.  iTunes responds with this enigmatic message:

Do you want to move the selected song (which was downloaded from the iTunes Store) to the Recycle Bin, or keep it in the iTunes Media folder?  Only files in the iTunes Media folder will be moved to the Recycle Bin.

I wasn’t born yesterday, but I don’t have a clue what this means.  I own this song: iTunes even knows that I bought it from the Apple music store (a fact that I had forgotten.)  I don’t know, in the context of iTunes, what a Recycle Bin is; I just want to remove the symbolic link.  I’m not really clear, either, what the “iTunes Media folder” is.  I have two links to the same object; I only need one (why would I ever need two copies of an identical song?)  Why do I have to choose between these incomprehensible options?

Amazon’s Cloud Player, on the other hand, behaves exactly as I expect.