iPain

Transferring iTunes from my PC to my Mac is a pain in the ass.

This is not my first time to transfer iTunes/iPhone. First off, this is my second iPhone. The first one was the original iPhone. The second one was the iPhone 3G. That upgrade was pretty flawless. Through iTunesPC I was able to convince apple that this was an upgrade, and so it transferred everything to the new iPhone. Then, I moved to a new PC. I literally copied the My Documents folder from the old PC to the new one, including My Music, which includes iTunes Music, and synced my iPhone 3G with iTunes on the new computer. Viola. I can't remember any problems with any of these other than minor issues I expected. But going from PC to Mac has been a royal pain.

First, not all of my music on my PC was in the iTunes Music folder (I thought it should have been, but I guess in some cases iTunes leaves legacy music in its original location when you switch to it from Media Player or RealPlayer or whatever). Because this can happen, one web site I found said that you should "consolidate" your library before transferring it from a PC to a Mac. This apparently forces iTunes to import all the music into its structure, making a standard library on the Mac. But iTunes told me there wasn't enough room on my hard drive to consolidate. I think I had 14GB free or so, and there were apparently 20GB or so of referenced media that lived outside the iTunes Music folder.

Second, because of issue number one, and because I wanted to do everything by the book, I decided to do an iTunes backup and restore. That actually seemed to work quite well. Time will tell. But I have the same complaint lots of iTunes users on the Net do: why can you only backup to CD/DVD? I'm glad that I now have 5 DVD's with my iTunes library backed up. Maybe I'll need those for something else again. But I wasn't glad to spend the 5 hours backing up and restoring.

So I gave iTunes a quick runthrough. I have lots of music and not a lot of videos or TV shows. I hae a few podcasts. All looked good.

And now for the moment of truth.

I plugged in my iPhone 3G. The first thing I noticed is that it didn't pick up the sync settings from the phone. That makes sense when you think about it because apple considers the computer to be the master and the phone/pod the slave. So I spent a few minutes checking boxes to sync music, video, podcasts, applications, contacts, etc. I was actually concerned that I wasn't getting the settings the same as on my PC, so I unplugged from the Mac, plugged back into the PC and reviewed. Then I had to start over. I was basically happy about the settings I made, so I hit Sync.

The first way iTunes scared me was with a message saying I had two choices: (1) Cancel, or (2) Erase this iPhone and replace it with contents from this computer's iTunes because each iPhone can only have one computer as its sugar daddy. I gulped and chose (2).

That seemed ok, except it got to the end and told me some of my content was not authorized on this computer. It was a copy of The Shack application, which is an eBook about a guy who supposedly spends a weekend with God in a Shack. It was a copy loaned to me by a friend. He typed in his password on my iTunes to "authorize" that computer. I need to get him over here I guess to authorize the mac. Problem is he lives in Atlanta. So I hit Cancel to ignore that. I can do without that.

But then it gave me another warning, a yellow one this time, about some of my applications not being authorized. Fine. I'm sure it's easily resolved. There were only two it complained about. I looked down at my phone to make sure everything looked ok except those two apps to my horror. All of my applications were GONE. Except the two apps it complained about. I thought maybe the sync died at those two apps and thus didn't finish, so I synced again. That's exactly what happened. The second pass it complained about 34 apps. The third pass it's up to 39.
Anyway, they're gone. And remind my why they're not authorized on this computer? Isn't that the reason I backed up and restored the library instead of copying it over and mucking around with the XML-based configuration files like I read about in the mac gurus website?

My wife just called me. Her picture popped up like it was supposed to. But her ringtone was some stupid apple default. Gone. Maybe if I keep syncing and syncing it will finally get most of my stuff back on there, except the applications. What a buttache.