Migrating iTunes from Windows to Mac OS X

I've had an iPod since December 2004, when I received one as a gift for Christmas. It was the first Apple product I ever owned, and it was responsible for me starting to take Apple seriously, something I had not done previously for a number of reasons. Anyway, that's just background to this factoid: I had an iPod before I ever owned a Mac, so my iTunes library has been on a Windows XP box since day one.

I want to decommission the aging monolith that is my Wintel P4 real soon now, so I set about moving my iTunes library from Windows to Mac OS X. How hard could that possibly be? Five minutes on Google lead me to believe, “Not too hard”—I came across not only an article describing how to do it, but official Apple support article 300173 entitled ‘How to use your iPod to move your music to a new computer’. This was going to be easy.

Of course, it wasn't. I made it as far as the subsection entitled ‘Is all the music together?’, step 6. From the Advanced menu, I selected Consolidate Library. There was briefly some consolidation, and then this:

Outstanding. In what universe does this qualify as a useful error dialog? Déjà vu.

There are at least two problems here.

1. The first is completely obvious: For the love of god, which file name was invalid or too long?
2. The second you'll have to take my word for: the consolidation operation aborted at that point, leaving (as far as I could tell) some of my music inside the iTunes Library, and some of it in its original location.

If either of these problems hadn't occurred, I could have moved on. If I knew which file was problematic, I could have changed its name. If consolidation had just soldiered on or it just reverted to the original state, I could have thought about a different approach.

To say that I was disappointed with how things were going at this point wouldn't really adequately convey my mood.

I had heard about software which could extract music from an iPod, but I had never tested any. Actually, I didn't even know the names of any applications. Google sent me to Senuti. Senuti certainly had no trouble finding the music on my iPod—all listed and organised as advertised, even the metadata (rating, times played, and so on). It also had no trouble transferring that music to my Mac Pro. What I couldn't get it to do, and what was going to be a deal-breaker this time, was transfer that metadata over to iTunes on the Mac Pro. I rode the change a preference–extract–check–delete merry-go-round for a few hours. I transferred my 20G music collection off the iPod about six times. Senuti could see the metadata, it just wouldn't pass it to iTunes. Then, sometime after midnight, eyelids propped open with matches, I somehow noticed I was running Senuti 0.50.1, and there was a 0.50.2b3 (a beta release—I had downloaded the latest stable release). I downloaded. I installed. It worked.