Sad but true -- If you listen to lossy files or phone DAC's you probably absolutely get worse actual sound quality than that 37 year old walkman. far better sound. It's not even close. I mean, no where near the quality that your phone's DAC can achieve. The accuracy of digital is something no cassette could have ever touched.
Tape hiss was a thing-- but it didn't change the sounds of the instruments or the soundstage. It just put a mellow hiss below it, especially noticeable between songs or in very quiet passages.
Wow and flutter was a thing-- but our brains adjusted for it's slight variations better than it does trying to reconstruct tonal loss and ignore digital artifacts. lol
You could also can make your own mix tapes playlist today without having to waste enormous amounts of time recording in real time, own the media if for some reason you want to fill your house with needless stuff, it's still a perfectly viable option, see the artwork (small, granted) now visible in beautiful high resolution and support the artist record company today, just like it would have back then. Of course, the record company will use a lot of that money to bankroll tours which pay large sums to the artists, so today, like then, it's indirect support of the artist with a single purchase of their music. Or you can stream it, or watch it on YouTube which to date has sent something like $3 billion to the recording industry, money that would have simply not existed in the days of recording your music to a cassette from the radio.
The good old days?