PC to Mac Migration, Part 2: iTunes Media Transfer

Tackling the transfer of iTunes media from the PC to the Mac is complicated by the fact that not all data in iTunes is stored within the file itself. Date last played, ratings, number of plays, and potentially even album art are stored via an XML file. Simply transferring the data files (i.e., the MP3s and AACs) will not retain this data.

From PC to PC (or I believe Mac to Mac), it’s easy if you store the files in the same place on both machines. Bring up an “empty” iTunes on the new box to establish the data’s location, then shut down iTunes and replace the empty iTunes directory and files it created with the ones from the old machine. In fact this is what I did in “reassigning” my PC to another member of my household.

But the above won’t work from PC to Mac (or vice versa) because the libraries cannot be in the same place. If nothing else the PC’s slashes in the directory path are foreign to the Mac, which uses colons.

Researching this a bit, I found two possibilities to bring everything over intact. One uses the iPod itself, the other requires editing the XML file (read the comments). To be honest, I wasn’t crazy with either possibility. It seemed like a lot of work (and chance of failure) for what should just be an import of data files. In fact, some of the various suggestions I saw seemed like overkill to me. So I took a serious look at just what I’d lose if I avoided either technique.

I don’t use “Last Date Played” because I’ve found it terribly unreliable. I created a playlist to avoid recent songs based on this date, and found it playing songs I’d heard only a week ago. I’m not saying it’s broken, maybe it doesn’t register the date unless the song plays all the way through, so if you hit next track when there’s five seconds left it doesn’t count as played. If true, maybe that makes sense, but it also makes the data worthless to me. Likewise with “Number of Plays”, though I never had a desire to use that field anyway. Ratings and Album Art, however, are critical to me. Almost all my playlists are based on ratings, and album art is an integral part of the cover flow and album views, as well as an enjoyment for when music plays via Front Row, my G5 iPod or iPhone. I won’t do without it.

In considering the items I determined to maintain during the transfer, album art is the funny one. It’s funny because the files themselves will store cover art, so it shouldn’t have been a problem. The issue is that if iTunes gets the album art for you (a great feature) it doesn’t plug it into each file, but rather saves the artwork separately and references it instead. I suspect they did this so that they could scan your entire library and update the artwork very quickly, instead of having to update every file. That’s fine, except it means if you transfer the file without the associated art and XML references, you have no album art.

The good news for me is that even after iTunes added the capability to get album art for you, I still followed a procedure of copying the art from one file and manually updating the entire album with it. In other words, I’d let iTunes get the art for me, but then I’d update each file myself. This only takes 15 seconds after adding a new album, so it’s no big deal. While I suspected there were some albums on which I’d probably forgot this procedure, and for which I’d have no art after the transfer, I figured it would be a relatively small number so I’d just get them manually.

As for ratings, I got around this issue pretty simply. I saw methods suggested using exported playlists and XML files. I saw no reason to do that much work. On the old PC, I used a smart playlist to find all songs with one star, then did a mass update to add “1star” into their comments field. I did the same for “2star”, “3star”, and so on. The comments field is in the file, so when the data is imported into the new system I’ll reverse the process.

Since all but one of my playlists is a smart playlist, I wasn’t worried about them since I’d just re-enter them in the new iTunes, and they needed a bit of an overhaul anyway. The one manual playlist I have was something I wanted to preserve, and I handled it just like ratings. I selected all the songs on the old PC and mass-updated the comments with the playlist name. That made it easy to find them afterwards and re-establish the playlist.

One thing to note is that another reason I did not take great pains to preserve everything is that I felt it was time for a little “Spring cleaning” on my media database. Over the years garbage tends to accrue, and this was going to be a good time to start fresh, something I’d be reluctant to do if the impetus of a new computer didn’t trigger it.

Comfortable that I’d preserve what I didn’t want lost, I opened iTunes on the Mac and, after setting my preferences, etc. and authorizing the machine for my iTunes account, I used Add to Library and chose my entire iTunes directory off a backup from an external USB drive. It imported my 30-odd TV shows, 2 movies, dozen or so podcasts, 1 audio book, and three iPod games just great. It also imported about 7,250 songs. That last bit was odd since I only have 6,850 songs! The entire import process took a couple hours.

The good news is my decision to do some “Spring cleaning” was justified. As it turns out, when I searched for duplicate songs I found many that had got themselves in different folders, etc, and so were imported twice. I was carrying half a gig or more of extra songs on my old machine and never even knew it! The fresh import brought these to light, and I cleaned them up with the help of the Show Duplicates in the View menu (by the way, why is it considered a duplicate even if the albums are different?). After addressing duplicate songs, the song counts between systems were in line. The process of weeding through several hundred duplicates took an hour or so. At this point I had a “fresh” iTunes database ready to start adding things back to.

I started with album art. I flipped though cover flow to look for any missing covers and, as I suspected, there were a few. I’d say of my 634 albums there were perhaps 35 that had “lost” their artwork in migrating to the Mac. Not too bad. I went to my usual cover art site, and dragged the artwork into the update dialog selected for all songs on the album. This took maybe a half-hour.

For my ratings, I simply reversed my earlier process. I setup a smart playlist to look for all songs with “1star” in the comments, then selected them all and right-clicked to apply a 1-star rating. Then I did the same for the other star levels. The whole process took maybe two minutes.

For my non-smart playlist, I searched for all songs with “Patio” (my playlist name) in comments, then drug them to the sidebar to create the playlist again.

Finally, there was the matter of my smart playlists, which I entered by hand. There were many playlists I had created but didn’t use, so this was a good opportunity to start fresh and create the ones I really used. I had 32 playlists before, and cut that down by a dozen; the process took an hour.

And that was it.

If I hadn’t already made a habit of embedding album art into each file, then recovering artwork may have been difficult (depending on how much could be automatically re-applied by iTunes on the new machine). The rest was pretty straightforward. If you must have the XML data for whatever reason, there are the procedures I mentioned above, but I’m glad I avoided them. I kept what I needed and “cleaned up” some stuff in my iTunes database I didn’t know was there. That’s a good thing from time to time.

From the time I started the import until the entire process was done was roughly 5 hours. This includes over two hours for the import process itself. Not too bad. Sure, it’s tedious work, but I won’t need to do it again for many years, and it’s not difficult. Besides, if the numbers are kept relatively small, as mine were, doing some cleanup manually, one time, can be faster than trying to avoid the manual effort altogether. I believe that was the case here.

OK, so was I ready to sync my iPod and iPhone? No, not quite. Everything was in place except photos. I only have about 50 synced, but I wanted them ready before I turned over the iDevices to the new Mac. Coming up in part 3, I import all my photos and have some comments about iPhoto 08.

4 thoughts on “PC to Mac Migration, Part 2: iTunes Media Transfer

  1. Neil,

    Thanks. I figured that’s what it was.

    I think they should have been more practical about it. They should trip the date when the song is maybe 80% played, or some other level short of an absoulte 100%.

  2. You’re correct that iTunes doesn’t register the date unless the song is completely played. I click near the end of the timeline to complete the song which updates the Last Played field.

  3. Fixyourthinking,

    No. Almost all of my music (98% of it) is non-DRM MP3. That doesn’t solve the problem. I needed the scenarios in my article to preserve certain data associated with the files, but not contained within them.

    For better or worse, I described the whole process in detail. Ultimately, I did just take a backup of MP3s and Add them to iTunes, but that alone, without the rest of what I documented, would have left me without my one manual playlist (which would have been nearly impossibile to recreate exactly), and also without my ratings (over 3,000 songs rated, getting those back might jave taken days!).

    It sounds harder than it was. The tasks were mundane, but very basic, and had no real chance of failure, unlike some of the methods suggested to avoid them.

    Fact is, when you swap platforms there’s getting to be more and more tools to assist in the process, but some “cleanup” will be necessary.

  4. “And that was it.”


    The other solution for iTunes media transfer? Don’t buy DRM’ed music or if you do – convert to CD and back to plain old MP3.

    Then all you have to do is back the Mp3’s up on a hard drive and drop the whole hard drive onto iTunes.

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