Thanks to those in the nomenclature thread, I was finally able to identify the models of Walkman that meet my needs. When I found this listing (albeit maybe a bit over priced) I jumped on it because it seemed to be the best starter. That and because it seemed leagues better than the bulky Jensen I've been struggling to carry around. So here's my first (as an adult) Walkman: the WM-GX788. The aforementioned Jensen shown for comparison.
That is a bit like comparing a Yugo with a Cadillac. If you worked out the inflation adjusted cost of each one there would probably be a similar ratio. Of course there aren't any new players of the quality of your Sony being made these days.
To be fair, "overpriced" is relative. I certainly don't think the price was bad. Truthfully, few prices are too high for the perfect item. This just isn't the perfect one, yet. But like you say, the quality is there and to me the upgrade is definitely worth the price of admission.
Welp. About a week in and I am pretty pleased. At first there was a bit of warbling on recordings, but after a few days and extensive running of the mechanism. That seems to have disappeared. The buttons aren't perfect, a bit shallow and small, but the audio cues are a nice way to affirm a blind, in pocket, press. It's nice to have a recording radio running off of a AA.