It was AWESOME for the time it came out, especially as a cassette replacement.
Cassettes were fragile, made all kinds of noise with tape hiss, bulky (carrying more than 2-3 when commuting was a headache), at best you had "music search" which would fast forward to the next gap in the program otherwise there was no random access or shuffle, they could be reused but I always found this to be less than desirable without using a degauss gizmo or recording white noise over the tape and then re-using it.
The deck would edit (delete songs, trim songs), you could title tracks and get exact MM:SS readouts (no more mix tapes with awkward spaces at the end), the media itself were compact so carrying a half-dozen commuting wasn't a hassle, the media were far more durable and reusable.
About the only thing I thought was "bad" was that duration seemed to max out at 74 minutes (I was a C-90 cassette user) and the walkman unit that I owned seemed to be a little heavy on batteries, but that wasn't a huge issue for commuting (I swapped in fresh NiMH AAs daily).
Totally obsolete now. It's too bad Sony didn't wise up and make the Walkman units USB compatible for disc read/write and let them play MP3 files. I would have kept using mine for a long time as 160 megs would have made for a decent number of MP3s.