I lived through that period, too. Tape was never a long lasting medium. As you listened to your favourite albums over time, the tape would stretch and the must would sound different over time. Especially if you left them inside a vehicle where they overheated. It was inevitable. And there was the horrible warble of the batteries in a walkman when they were getting weak. By the time 1990 came around portable CD players were available, and a few years later when anti-skip CD players they were far better audio quality than portable tape players ever were.

What I really wanted in the late '90s or early '00s was a DVD MP3 player. Then I could've carrier my entire music collection around with me.