"it doesn't seem possible that such technology is already considered vintage."
Actually, it seems a little depressing. Although one way to console oneself is to think that the technology world moves so fast now. Even 5 years old can be OLD now.
I remember the Walkman and various clones when I was in high school. (Although, technically, they were banned in school, I'd see them about. I wonder now if the ban wasn't more to protect the school: "Well, Mrs. Jones, it's sad your son's Walkman got flushed down a toilet, but it shouldn't have been here in the first place. See the rule book, page 47, rule 397, subsection 7.) I never had one myself, and I never recall having had any desire to own one. Possibly I saw no real value for me. Possibly it was to be contrary, and go against what the herd was doing.
I got a Kenwood Walkman-style cassette player that appears to work, but have not actually tried. One of these days.... I seldom use cassette these days.