Speaking of old Windows and CDs, Windows had some crazy trick to turn CD-R (not CD-RW) into rewriteable medium. I'm guessing they simulated a regular file system on top of an append-only representation. I never dug into the details back in the day, because I never used this feature. Unfortunately, IIRC, this trickery was enabled by default when copying files to CDs - which was a problem, because nothing else could read it. This caused me an unending stream of calls from friends and relatives, who all tried to burn some family/vacation photos onto a CD-R, in order to view them on their TVs, but the CD readers for TVs couldn't parse the format.
Oh, the trick of placing the table of contents on the outtermost place of the written area, instead of the beginning of the CD.
I think you were supposed to write a pointer at the original place, so the driver would know to look again, but outside in. Video CD players often didn't support that pointer.
But actually, Windows was quite a latecomer on that feature. It's just that its UX was horrible so people would never know what option they choose, on other OSes (and other Windows software) people had to actually decide to use it.
I remember also another quirk — you could burn CDs that various appliances will read, and you could do it such that you're able to add more files later, but you had to do that through Windows Media Player.
