Why not get him a tiny cheap media center PC or chromebook or such? You could probably even do this with a Raspberry Pi. Hook it up to a nice set of PC speakers

Why not get him a tiny cheap media center PC or chromebook or such? You could probably even do this with a Raspberry Pi. Hook it up to a nice set of PC speakers. Set up remote access to it for yourself. Then you can either download a selection of music to it or set it up to play from a streaming service just as you would on your own PC. If your dad wants to turn it on or off (or the caretakers need to), he can use the volume/power knob on the speakers. Or if he likes a popular genre of music (classical? Classic rock?), maybe just get him an FM radio?