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I was using a Mac Book Pro OSX 10.6.8 and had burned a lot of my CDs onto it. I had never bought anything from the iTunes store. When opening iTunes one day I saw everything had changed - playlists had disappeared and I when I went to Finder the bulk of my music was bundled under "Unknown Album". As I have the music on my iPod I continued using that; since I never buy songs from the iTunes store I just left it.

Now I have a new Mac Book Pro OSX 10.8.5. I used an external HDD and Time Machine to back up the old Mac Book and still have the back-up that predates the problem.

My question(s)

  1. Can I transfer my tunes on the iPod to the new Mac Book (none of them are from the iTunes store)?
  2. Is there any other way of fixing the problem?
  3. Is there an alternative to iTunes that allows me to burn my CDs onto the Mac Book, organize them into playlists etc and copy to my iPod?
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For what you asked first, here is what you get first:
https://www.macupdate.com/app/mac/35334/detune

DeTune is an App that helps you get Songs from your iPod.

For everything else regarding Organization:
Open iTunes and hit CMD+,

You should see the Settings, if not go to The Menu and click iTunes -> Preferences.

Here is all I know after I struggled with iTunes (a lot):

You can specify Import Settings on the first page of the iTunes Settings page. At the Bottom you can also say that you want to download the names of the tracks.

Regarding the Organization :

iTunes handles the media the way you specify it in the Advanced Tab inside the preferences.

So you should check on that via going to preferences -> Advanced.

You should see the place where all the media is stored. Also you should see checkboxes for the automatic management and the option to copy the media inside the iTunes Media Folder.

If you want make iTunes do the work, check both.

And well, that is basically all you can do to achieve what you want.

To better organize your media with iPhones/iPods there is no way around iTunes. It's simply the only App that can handle your device completely.

If you want to organize your media professionally, tag them manually or via great tools like Picard (from MusicBrainz), Metadatics, Tagger or something else. Organize it in Folder you like inside your Music Folder and don't let iTunes organize them. Then (if tagged correctly) drop them into iTunes.

To be sure you added the files, maybe add a Finder Tag to remember yourself in the future.

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