Can I add the iTunes Music Library (old) to iTunes Music Library?

Question

Hi, I'm asking this question on behalf of a friend and I don't want to give her incorrect advice ... She has an Intel G5 iMac running 10.5.8 and iTunes 9.0 (she has downloaded but not installed the iTUnes 9.1 update).
Her problem is that she has deleted certain songs from her 'Jane Doe's iPod Playlist' so that she didn't have those songs on her iPod - I don't know the method she used to do this, nor does she. However, it has resulted in those songs now not showing up in the iTunes music library on her computer. There's just an exclamation mark and a dialog box asking if she would like to locate the songs.
She asked me to help her out and I discovered that all these songs (there are dozens- more than a hundred - of them) are still on her computer in a folder called 'iTunes Music old' - this is a sub-folder of the iTUnes Music folder where the path is Music - iTunes - iTunes Music.
My question is this -
Is it possible to select all the albums in this 'iTUnes Music old' folder and simply drag and drop it onto the iTunes Music folder (after making sure that the location I'm dragging and dropping to corresponds to the location for her library as specified on the advanced tab of preferences) so that the songs will be back in the default library?
It seems to me that it should work but I don't want to be responsible for the person who loses all her music for her if it doesn't.
I would really appreciate someone who knows their way around iTUnes telling me the best way to sort her music and whether or not she should install the 9.1 update before or after reorganising the library.
Cheers
Tricia

Answer 1

Her problem is that she has deleted certain songs from her 'Jane Doe's iPod Playlist' so that she didn't have those songs on her iPod - I don't know the method she used to do this, nor does she. However, it has resulted in those songs now not showing up in the iTunes music library on her computer. There's just an exclamation mark and a dialog box asking if she would like to locate the songs.
If you're seeing the , that's generally an indication that media files (the mp3 or m4a, etc., files) were moved using Finder. They were moved or removed and the iTunes library wasn't able to keep track of where they went. If this is an old machine that she's messed around with, it can be a bit of a crap shoot trying to figure out where the stuff should go (iTunes is quite unhelpful in telling you where the music for the broken links was expected to be ... you can take some guesses, but iTunes 9 and iTunes 8 use different folder structures, so getting the stuff in the right place can be a nuisance).
Is it possible to select all the albums in this 'iTUnes Music old' folder and simply drag and drop it onto the iTunes Music folder (after making sure that the location I'm dragging and dropping to corresponds to the location for her library as specified on the advanced tab of preferences) so that the songs will be back in the default library?
Surprisingly complicated question. If you were confident of where the music files should go, you could try moving them (safer, copy them) to your current iTunes media folder and if you drop them in the exact same spot they were before, your broken links problem will be solved. It's a long shot, though.
There are apps out there for rebuilding libraries, but if you don't have extensive playlists that would take forever to rebuild (or you don't have lots of ratings or things like that which you are trying to preserve), I'd personally be inclined to rebuild her library from scratch by:
Create a new library by pressing and holding down the option button while you start iTunes, keep holding the button down until it prompts you to create a new library.
Go into the "Advanced" section of the "Preferences" screen and tell iTunes to (a) keep your folder organized and (b) to copy music to the new media folder.
Use the "Add Folder to Library" command on the "File" menu to add the music to your iTunes Library. This will copy the music to the new folder you specified in the previous step. Repeat this for her old iTunes folders (sounds like she might have it in different areas). Nice thing is, you can select some common parent folder (e.g. your parent "music" folder) and you'll only have to do this once.
Once iTunes is done copying music to the new media folder and has rebuilt the new library, you can clean up the old music media files that it sounds like are scattered about on her machine.
Again, I personally lean towards just rebuilding the iTunes library, allowing iTunes to organize the files like it wants, and then rebuild your playlists. But, if you'd rather try to repair her old library in situ, then you'll want to check out some of the apps designed for repairing broken links in libraries. Let us know if you want to do that and we can point you to some apps that might be able to help.
It seems to me that it should work but I don't want to be responsible for the person who loses all her music for her if it doesn't.
It's kind of hard to lose the music unless you do something nuts like drag stuff to the trash without making sure you've got a copy/backup somewhere. In fact, go ahead and have her back up her machine before you start. And when you're all done, and you've confirmed that everything is great, do another backup.
I would really appreciate someone who knows their way around iTUnes telling me the best way to sort her music and whether or not she should install the 9.1 update before or after reorganising the library.
Unless her version of iTunes is archaic (v7 or earlier), I'd suggest fixing her library first, and then doing the upgrade. Let's not add variables to the situation. Also, I don't know what the iTunes upgrade process would do with the broken links in her existing library.
Frankly, there are enough bugs/problems with 9.1, you might want to wait until 9.1.1 comes out anyway. I personally regret doing the 9.1 upgrade. It works, but I'm working around various bugs. And some people are having very serious problems. If you absolutely need 9.1 (e.g., iPad), you can do it and you'll probably be fine. But unless you need 9.1 for some reason, I'd wait for 9.1.1 release.