Subjectively, I've always felt that vinyl produces the best sound and cassette tapes produce the worst. My tapes never lasted long and they didn't sound great to begin with. Then again, I played my favorite songs over and over while skipping the duds. I'm sure all that rewinding and fast-forwarding didn't help. Every Walkman I've owned has been a real pleasure though. I dropped them many times, but each model kept ticking along.
You are correct about this topic as subjective. I have some music files that sounded crisper than others. Maybe the difference was made during the encryption process to become an MP3 file. I also have some difference of volume as some of my music is louder than others, even though I have set the volume in just one level.