I remember late 80ies I was just over 10yrs old and got my first Sony Walkman from my dad. Man was that a masterpiece, simple but beautifully sounding. Never ever afterwards I had bought anything from any other brand to play my cassettes! The last walkman I had was of size of the cassettes box, seriously, with just a slight bump for one AA battery, that gave me over 15hrs of delicious playback. Fully auto/rev, song search ff/backw. etc, crazy!
I had such a hard time when switching over to CD and later mp3 players, I felt like I was hard pushed by the industry when the cassettes started getting more and more expensive ?.
From my experience, the key to the sound was making right CD->cassette recording. I had used friends Akai system for that, then always prefered listening back from a cassette rather than directly from CD. Those times...