gifting tunes to remote computers
I have a dear friend in another state whose choral and opera music career has been halted due to traumatic brain injury (TBI). He was beaten within an inch of his life. His wife is trying to get help creating playlists of musical pieces that have significance to him on her iPod for music therapy. She doesn't have time to go through his huge collection, select and download pieces through the computer to the iPod. She has put out requests for specific pieces that she thinks would be helpful but so many classical pieces' files are too large to send. I personally don't have the software to compress them, though I wouldn't mind finding an EASY compression program that would to it. I have tried several and they are way too complicated intended for business file sharing.
Is there a way I can gift her pieces I find in iTunes and send them to her iTunes account?
iOS 7.1.2