This is one of those “they were so concerned with if they could do it, they didn’t stop to think if they should” sort of things.
Portable cd players were never actually that portable, because cds are just big. Minidisc players sure, but those never really caught on. MP3 players, however, caught on because they are small and easily portable, and the library doesn’t take up a binder.
With current technology you could make them a lot better. Basically put 700mb of flash memory on the player and rip the whole thing as soon as you put the CD in, then play from flash. But then you get back to why you would want to do something like that again.
I had a Sony atrak 3+ player back in the day (around 2003-4, probably, because I used it at work) which was just an mp3 file compression alternative served up on a special cd player instead of an mp3 player… they tried.. anyway I had a re-writable disc that I’d add stuff to whenever I downloaded it, and I think the one cd had like 1800 songs on it or so (and lots of space left)
That didn’t skip, even working a physical job, unless I banged it against something. Part of why I got it. But when I put regular discs in, they would skip a lot if I didn’t have it laying flat.