For my blind and very forgetful 93 year old Mum, I ripped her CD's a few years ago using CDEX (didnt need to worry about album art, detailed tags etc), built a headless Linux mini PC and wrote a small shell script that auto restarts on power on (if she remembers to turn the PC off) and it remembers the last track played on power on.
Tracks are played in a random order.
So its basically one big arsed playlist that cannot die, be killed or stopped and plays over some small powered PC speakers.
She loves it...never has to touch it (aside from turn the sound knob up/down on one of the speakers).
She drops off to sleep during the day in her chair and wakes up and its still going. I actually think the PC hasnt been turned off for years.
If your Dad's music is on CD and you are willing to rip them, I can help with the mini PC setup (if needed) and provide the simple script, if this solution appeals.
Peter
PS. In fact, to make it really simple, I can provide you with a USB stick image from which Linux can boot. You can do your ripping from Windows running on the PC (if thats your bag) and I can set the USB boot to mount the windows volume where the music is (say make a D: drive just for the music)... or if you are ok with Linux then just install as normal