A woman called and wanted me to transfer all her songs from an iPod to an iPad. I thought it would be straight forward but in my case, no such luck.
So online I went searching for information about transferring the files more manually. First I downloaded a program called PodTrans from iMobie.
I hooked up the iPod and followed iMobie’s guide here: http://www.imobie.com/guide/anytrans/transfer-media-files.htm to transfer the music files to my hard drive. 972 songs altogether. But after this I couldn’t find the option to transfer back to the iPad. Eventually, I found and followed the info here: http://www.igeeksblog.com/how-to-sync-songs-to-iphone-or-ipad-without-itunes-library/
Half of the songs in iTunes where greyed out and so were the ones on the iPad (they where unplayable). Went searching online for some help but found nothing useful. So I decided to start over. I deleted all the files from the iTunes music library. Then I decided to drag the folder itself over and sync it up. And it worked.
I got there in the end and I guess all’s well that ends well.