Syncing services by their very nature need to be somewhat transparent. They need to happen in the background. Hitting “sync” every 10 seconds after you make a change makes for a poor user experience.

In the case of iTunes Match, the concept is relatively simple:

1. After subscribing, music from iTunes will be available for you to stream to any device you are logged into. Your playlists and albums will all be at your fingertips. If iTunes does not have your music, they will upload it and store it for you to provide the same results.
2. If you add music to iTunes they will update the music in the cloud to reflect the changes.
3. If you change music on one device, changes will propagate to all your other devices.
4. This will all happen seamlessly without any intervention on the part of the user.

This looks really great on paper, but real life is rarely made of paper.

I’ll readily admit, I’m not “most people.” There are probably a lot of people for whom this works really well. It has not been so for me.

I have roughly 12000+ songs in my library. ~1500 of them are from iTunes or other CDs. ~9000 of them come from video game soundtracks or remixes. (Yes, I know…)

So yeah. Apple had to upload a lot of my music. What’s the problem.

I’ve had several problems and all of them come down to the fact that iTunes Match has no user interface for me to go in and make changes or choose settings or anything else. Arguably, it shouldn’t have these (it doesn’t.) Arguably, it shouldn’t NEED these things (I think it does.)

Duplicate Songs.
I have some songs which iTunes claims are duplicates. It refuses to upload these to iTunes Match.

This confuses me, because playlist wise… If I have the same song in a playlist twice, it shouldn’t be a problem. It’s a second instance of a song I already have. But somehow, I have two copies of the same song imported into iTunes. I always assumed that if I copied a song I already had into iTunes it was smart enough to not need to copy the song again. (Sometimes I thought it appeared smart.)

So somehow I have two copies of the same song. Big deal. So how do I deal with this?

Well I can “keep duplicate” or I can “delete duplicate”. What does this mean? Does it delete the file? Where is the duplicate? If one of these songs is in a playlist, I’d like to keep the song in the playlist. But now I have to manually search out several dozen duplicate songs and put them in the right playlists? (Why did the “find duplicates” option disappear from the new iTunes?) What if I can’t find the supposed duplicate? Do I have to recreate all my playlists?

Nested Playlists.
Because of how my library is setup, my video game music lives in it’s own little folder, separate from the other stuff I listen to. So naturally, any smart playlists for my game music should only pick up game music. With so much music I have playlists to keep track of my most played songs, my highest rated songs, songs I have yet to play, and songs I really like but haven’t listened to recently. All of these playlists rely on my folder structure so that only songs from my video game soundtracks list show up in the playlists.

But on iTunes Match, these playlists are empty. I don’t necessarily want/need the smart playlists to be auto updating. But why can’t the playlists be updated statically?

This Playlist is not Eligible
I have a few odd song types which I should really sit down and convert into CBR MP3 files. However, if a playlist contains one (or more) of a “non-eligible” media type, the entire playlist is rejected from iTunes Match. Let’s not throw the baby out with the bathwater here.

And finally: Where’s the master copy?
Since signing up for iTunes Match I have added new music to my library. Often times I will add it to a playlist I already have setup. In more than one instance, after adding the music to my playlist, I will return later to find that it is no longer in the playlist I put it. The music is still in my music library, but it’s not in my playlist.

I will admit. This might be partly caused by the horrible, horrible internet service I am stuck with. And *maybe* this was a bug that was fixed with the latest update. But this leads me to my concern.

iTunes Match was built to be the master copy. For me, my iMac is the master copy. So when I add music to iTunes, I want to see where it goes and I want it to stay there. But Apple could very easily tell my iTunes to match the cloud and take whatever it wants out of my playlists.

Is this really happening? I don’t know. But I know that multiple times things have disappeared from my playlists. Hopefully, this is a bug that is or will soon be fixed.

Yet this all comes down to a transparent interface. No where can I go and see how iTunes match is coming along. No where can I go to tell iTunes match to check/upload a playlist. No where can I go to tell iTunes match to ignore a song or playlist. (I would love to make a folder in iTunes for temporary file conversions or testing and not have iTunes upload the songs to the cloud.) Where can I go to tell iTunes to take music out of the cloud?

iTunes Match is a phenomenally convenient and theoretically seamless idea. But it was designed without a user interface. It was built to be seamless in an environment that could use a few seams. I have full days when the little cloud icon in the corner of iTunes is loading away or the bar along the top says “Matching your music…” for hours, even though I know it already told me I was up to date. How can I check up on that? How can I see the progress? As a power user, I’d like some more options. And I know… Apple’s bad with options. But they also don’t seem to be very good at being seamless. So where do we draw the line?