Indeed, some models are reselling for extremely expensive prices nowadays, it's a bit crazy. Especially since digital is just much more convenient, but it can feel nice to have some physical media

Alternatively you could look into a cassette deck if you're not set on a portable player (one released before the 2000s, I don't think they make new ones at all anyways), the high or medium end decks tend to have better sound -- there's much less flutter/wow -- compared to portable players in the same price range nowadays, since they're less "cool". Still have to be pretty lucky to find good deals though