I Got a New Mac or How I Transfered iTunes

I got a new Mac!  Yea!

So excited - everything is supposed to work so much better on a Mac.  Right?

It comes with this fabulous automatic utility, Migration Assistant, that will move everything over for you.  Yea!

Beautiful - all my files seem to be here - they don't look as organized as they were, but I think it's just showing me that they weren't as organized as I thought they were because the folders are now mixed in alphabetically with the loose files.  Another task for another day.

So, I go to open iTunes - the ONE thing I'm NOT worried about because, after all, it's an Apple product.  But oh, where are my playlists?

You know those lists that can take days to put together?  I call AppleCare because that's why I bought it.  They don't seem concerned that I don't have playlists and go find out how I can manually bring them over.  I bring over a couple while I'm on the phone and it seems to work okay so I hang up.

As soon as I actually go into one of them I find all these exclamation points next to my songs.  Turns out only about a quarter of my music actually made it to the Mac.

I won't won't bore you with the two days and five AppleCare calls worth of gory details on all the things that didn't work.  Let's cut to the chase of what did finally work.  These instructions assume that you have updated iTunes on your PC.  These instructions are valid as of March of 2013.

Keep in mind that I'm not a tech blogger - this is just my personal blog and if this can help you great.  If not, feel free to move on to someone more qualified.

1. In iTunes on your PC, click edit -> preferences then select "advanced" and make sure both the "Keep iTunes Media folder organized" and "Copy files to iTunes Media folder when adding to library" are selected.
2. Next, still in iTunes on the PC, go to File -> Library -> Organize Library and check "Consolidate files" then click "OK".  This moves your files to the right places and makes sure iTunes knows where they all are.  If it allows you to also check "Reorganize files in the folder "iTunes Music"", do that as well.  This step could take a while depending on how jumbled up your library is (mine was a mess!).
3. Now you can close out of iTunes (and if you aren't going to be using it any more on this PC, make sure you go to Store -> Deauthorize This Computer first).
4. In your browser, go to http://www.copytrans.net/#copytrans-tuneswift to download TuneSwift for $15.  You will need this to back up your iTunes with playlists.  It is worth $15 to NOT spend two + days trying to get iTunes onto your new Mac, trust me!
5. When you have TuneSwift installed on your PC, select backup.  You'll need an external harddrive for this step.
6. Going to your shiny new Mac and, if you've already opened iTunes, go to Finder (just click anywhere on your desktop) ->Go -> Computer -> Music and then use two fingers to "right-click" on the iTunes folder and select "Move to trash".
7. Now open a browser window and go to http://www.copytrans.net/support/how-do-i-restore-my-itunes-library-backup-file-on-my-mac/.  You will have to download the Mac Restore App but once you do you can plug in your external harddrive and restore your iTunes library exactly as it was on your PC.
8. When you open iTunes, just hold down the "option" key (the icons will dance) as you click on iTunes and it will automatically install the library you just restored.

I hope this helps someone avoid the frustration I went through.  As I searched, I found some instructions, but none of them got me all the way there.  These steps did.  I'm sure there are little, common knowledge steps I didn't include here (like ejecting your external harddrive), so please do use your common sense!