Can I use my nano to add missing songs to iTunes?

Question

I recently bought a MacBook Pro, and I've been trying to transfer my iTunes library from my old PC to my new Mac. I was having a lot of trouble with it, so I got in touch with Apple Support, who were very helpful, but nothing worked. In the process, any songs in my iTunes library that I hadn't downloaded from the iTunes store went missing. I haven't been able to find them, and neither could Apple Support. I still have everything on my iPod nano. Can I use that to add the missing songs to my iTunes library on my Mac?

Answer 1

Moving a library: Quick answer if you use iTunes' default preferences settings:  Copy the entire iTunes folder (and in doing so all its sub-folders and files) intact to the other drive.  Hold down the option (alt) key (shift on Windows) and open iTunes.  At the prompt to create or choose a library choose the copied iTunes folder. You would have to try really, really hard for this method not to work.
If this is to a new computer and you put the copied iTunes folder in the default location of Macintosh HD > Users > *User Name* > Music  then you don't even need to start with the option key held down, iTunes will automatically look for it there.  (Make sure there isn't anything already in the iTunes folder there that you want to keep since you will be replacing it with the one you are moving.)
Windows users see tip at: https://discussions.apple.com/message/18879381#18879381
Consider moving everything from your Windows PC to your Mac in a single move, including your iTunes library: About Windows Migration Assistant - http://support.apple.com/kb/ht4796 - Learn about how to use Windows Migration Assistant to migrate your files from a Windows PC to a Mac.