Oregon Trail held up well but, man, Kings Quest is brutal with the killing you and having to start over.

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

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!

I’d probably add “Save Early, Save Often, Save Multiple.” because there are so many ways to accidentally softlock yourself making the game totally unwinnable without realizing it until hours later.

There’s a reason most of us as kids started out with descriptive save names like `INNKEEP.SAV` and `BUYSLED.SAV`, and then halfway through the playthrough it's just `1.SAV`, `2.SAV`, `3.SAV`, etc. :)