Moving an iPod between PCs

Before Christmas, as late as December 23, my wife told me that she didn't want anything for Christmas, except my help in moving iTunes friom her old PC to her new PC.

Now, I didn't believe the "not wanting anything else for Christmas" bit - we weren't married yesterday - but I did take this as a clue.

The complication: Her old PC is hardly functional. She got her new tablet PC last Christmas. Apparently she has been using her old PC for iTunes, tolerating, barely, its slowness. 6 years old, and slow even when new. Network no longer working: wired Ethernet connector broken, wireless PCMCIA card non-functional. I would not be surprised if its slowness was due to malware, although McAfee's scans found nothing.

How hard can it be to move an iPod from one PC to another? It holds all of my wife's songs, not a subset. Surely I can install iTunes on the new machine, synch up, and be done?

Not so easy. Apple has not made it easy to migrate. Of course, things ae not helped by Apple's iTunes user interface, which I find idiosyncratic, differing from standard PC applications' UIs in ways that make it hard to figure out how to do things. For example, I went looking for the UI options to put the iPod into "disk" mode, but it was not until I googled that I found it.

I'll make a long story short, by NOT going through every wrong step I made. But I'll list a few.

Googling "moving ipod between PCs" found several pages, the most useful being:

(1) Apple support, http://support.apple.com/kb/HT1329. Useful as far as it went, although it was impossible to follow the instructions (a) because some were wrong, or at least did not apply to my wife's old iPod, and (b) some could not work, because, for example, they suggested consolidating the librray on the old PC's disk under the iTunes' Music folder - but my wife's old PC disk was full, and did not have the space required for such consolidation.

(2) The DIY article http://www.makeuseof.com/tag/how-to-move-music-from-your-ipod-to-your-pc-in-5-easy-steps, which gave the most important clues, although it ommitted how to transfer playlists,. Again, I suspect that some of its instructions applied to newer iPods than my wife's.

Early on, I tried iTunes ... Export, but on my wife's old iTunes this exported only an XML playlist file. Importing that onto the new PC gave me empty playlists. Apparently the new iTunes has "Export Library" versus "Export Playlist".

Early on, I tried just plugging the iPod in to the new PC. But there was no option to synch FROM the iPod TO the PC, only from the C to the iPod. I started being careful, not to lose the only easy to access copy of my wife's music.

When I plugged the iPod into the new machine, iTunes warned me that an iPod could only be hosted by one Library at a time. At first it also warned me about songs on the iPod that had been purchased from iTunes, which the new PC was not allowed to play until authorized.

My wife, of course, did not know what her Apple account was. Googling her gmail, I saw that Apple was sending email to my 9-year-old daughter, and my wife. Neither seemed to have Apple store accounts, although my wife's email did seem to have a MobileMe account. What the heck is a MobileMe account? I eventually signed my wife's email up for an Apple store account. But the warnings about unauthorized songs persisted.

Eventually, I got the old PC up enough to see that it was signing into iTunes with yet another email account. That fixed the "purchased songs" problem. But now the new PC iTunes just wanted to delete all of my wife's iPod.

I tried making a disk backup on my wife's old PC iTunes... 6 disks later, it hang. Unsure how complete the backup was, I resorted to the DIT technique.

I opened the iPod as a disk. I set folder options to view the hidden iPod files. I copied all of the iPod files, *.*, into a single flat directory on the new PC. (Actually, I searched *.m*; at first I searched *.mpg, but there were a lot of *.m4a, as well as a few MPEG-3 *.mpg downloads from NPR. *.* caught everything.) I made sure to tell the copy NOT to discard files with the same name, but to create extra versions.

I then imported these files into iTunes, using File ... Add Folder to Library. Having learned my lesson from the old PC, I had already set, per the DIY arrticle, Edit / Preferences/ Advanced / Copy files to iTunes folder and Keep iTunes Music Folder Organized.

This left me with the music files, but the playlists were messed up.

The smart playlists, e.g. "All songs by Jimmy Buffet" worked, but the manual playlists failed. I must confessed that I had hoped that the playlists would have some sort of content-ID, and would magically detect when the song was installed. Not so.

I reimported the XML playlist friom very early on. This time, they found the songs, and the playlists were populated.

This result in duplicate playlists. The smart playlists were almost identical - except for the versions that selected 100 random songs from a genre. The manual playlists had one empty playlist, and one full. Deleting the duplicates was straightforward.

Annoyingly, the "Purchased" (from iTunes) playlist was empty, and there was a manual "Purchased" playlist. But i could move the files back and forth.

Annoyingly, the "Recently Added" playlist was messed up, since all of the songs were recently added.

Wrapping up by authorizig the new computer, and de-authorizing the old PC. As you may recall, the old PC's network was dead, so that last involved minor hackery. Q: what does somebody do if their old PC is dead, dead, dead? Waste an authorization out of the limit of 5 PCs allowed to play a somg from iTunes?

Summing up:

1) I copied the music files as described in the DIY article

2) I transferred the playlists via iTunes' export XML format

3) Authorize the new PC using the iTunes account, de-authorizxe the old.

Fairly straightforward. And yet it took an embarassingly long amount of time to accomplish - many hours. I had pooh-pooh-ed my wife's request for help, but I can avow: this wasn't as straightforward as it should have been. Apple's support was incomplete and inaccurate.

Things would have been much better if there was a way to extract the playlists friom the iPod itself. The data is undoubtedly there..

Things would have been even worse if my wfe had used any of the iPod's other features - contacts or calendars or ...