Oregon Trail held up well but, man, Kings Quest is brutal with the killing you and having to start over.
As a kid who hadn't seen anything else, the mechanic of "save early, save often" made perfect sense to me (and I've always wished I had a similar mechanism IRL!), just as I imagine it did to the Sierra authors. And in fact I think there's a lot to like about it -- it's not "good game design", but imo it does provide stakes and a sense of danger in a way that the Lucasarts/etc stuff doesn't. But, yeah, a kid who's had more than passing experience with modern games certainly might not see it that way!
Totally agreed. Related, I actually wrote a satirical blog post on the brilliant but equally frustrating experiences of playing King's Quest IV: The Perils of Rosella when I was a kid. Just call me Captain Ahab because I hated that damn whale...
https://mordenstar.com/blog/kqiv