Not a problem now with digital media.
Still a problem. Digitally created works are just starting their clocks.
There are plenty of OLD works that will expire before their copyrights do.
And 50 years out, do you think there will be much backwards compatibility to play old formats? Will you still have a CD player in the age of chips, offsite storage of tracks, etc. If music was on floppy discs, you’d have a hard time even scaring up the equipment to play it. Let alone the codecs and players that are backwards compatibile. And the Digital Millenium Copyright Act will prohibit you circumventing that copy protection EVEN AFTER THE COPYRIGHT HAS EXPIRED.
The money goes to a handful of corporations. The musicians sold their stake in the music long ago.
And if someone who played an instrument in Boy George’s 1980s band is worried about not getting money from those recordings in 20 more years, he should try to figure out if those songs will even be POPULAR in 20 more years.