I bought him an iPod a few years ago, showed him how to use iTunes (he can use a laptop ok) and copy the music from CD's to the iPod.
However he has the grand total of one album on his iPod. So he doesn't really use it.
He still listens to vinyl but also has several Tivoli radio/CD systems around the house. I'm trying to think of a simple solution for him to get the music he wants at a reasonable price, and easily. About the only thing I can think of so far is to sign him up to google music or spotify, give him my old S3 which has a vertical dock, and leave it permanently plugged into mains and to the 3.5mm audio input on the Tivoli.
That way he would simply wake the phone, (wouldn't need a sim or security) and add music simply by searching for it. I don't think he's ready for any kind of remote system (IE streaming from a tablet or something like that)
Thoughts? Should be pretty cheap, just the cost of the subscription, and he doesn't really need to "move" the music around.