It seems to be both a question of the CDR quality AND the player usually. I have some that will only play on the external CD drive of my Mac of all things, which at least allowed me to rip a few, but not on any other players, a few that will play in my car and nowhere else (including the external drive), some that will play through good until the last 5-10 minutes, and then some that won't play on anything, and some that despite being nearly 30 years old still play fine the whole way through without blemish on any player.
I have that Proof of the Shooting CDR mentioned earlier and I wish mine would even play to the last 5 minutes. Its completely gone. Same with the Wilt/Augur 2CDR on Solipsism and a few others. OTOH, the K2, Azoikum, and Chaos As Shelter CDRs from Solipsism are still going great. I guess it depended on what brand he used. Same with the Knurl Panta Phei CDRs. Some still work great, some are kaput. At least those are all up on his bandcamp.
One that really sticks in my craw is Redrot-Cathedral of Filth. A great release, probably my favorite of all the Redrot material, but this was a case, I believe, where the CDR batch was bad even to begin with and all failed within a few years. But, in my case, I HAD ripped it, knowing it was failing, but then the hard drive I had put them on crapped out! So its lost completely. Incidentally, let me use this to call for a rerelease of Cathedral of Filth for my own selfish reasons, but also a a lot of Mr. Oppermann's material could use some reexhuming for the world. Seriously underrated talent.
Another one was the Azoikum/Lefthandeddecision split CDR that Live Bait put out. That was a case where I kind of forgot about it for a few years, then pulled it out to listen to one day, and I had no luck on any player. Never had a chance to even try to transfer it. I remember the LHD track being pretty awesome too.