I plan to do the same, but about 3-4x more stuff.
And if my kids response to that is anything like mine to my mother's music, they will barely ever listen to any of it.
I think this is more of an issue with headphones than with the inability to inherit digital files. (Which, as you note, doesn't exist.)
When I was small my mother would play CDs on a home stereo system. So if she was listening to music, I heard it.
This means that I'm familiar with and like some of her music. If she left me a pile of CDs I'd never heard, I would most likely not bother listening to them.
What I get now is how he used his albums to travel back in time to re-live glory days of when he was seeing the world and watching the effect his voice would have on people in different ports. Using your voice to make music is such a personal form of expression.
Understanding the music choices of your parents is one way of knowing who they were, often to some surprise after they are gone. I'm left with his albums now and they help me make that connection with the past and a renewed love for music back from the time when I was first learning it singing with him.