Taping one's own vinyl records and playing the tape in the car always seemed reasonable to me. But many people taped their friends' LPs and that, of course, meant that the music industry lost out.
Similarly with CDs. Transfer your own CDs to an iTunes store on your own PC would seem reasonable - but the unscrupulous could equally copy everything to a portable drive and sell it on.....
The greed of a few will always result in heavy-handed copyright protection becoming necessary.
Yoof of today simply won't pay 6/8 for a single 3 minute track!