Speaking of obscure, getting Washington to cut down the cherry tree by painting the fruit red got me stuck as a kid in Sweden. I hadn't heard the cherry tree myth (and now only through the game) and even if they gave hints in the dialogue, I didn't get those either. I don't even remember if I got past it or if I gave up.
I replayed the remastered game a couple of years ago on PS4 with my daughter who was seven years old, and this time the only thing I was stuck on was the cat puzzle with the squeaky mattresses. I read a blog post just now about that puzzle, and it's special because you use the Use verb on two different things outside of your inventory. You usually go inventory->world or inventory->inventory, but here it's world->world. So I had to look up that one solution in the whole game.
Playing as an adult, it's much easier to keep in mind what clues you have and what the open puzzles are. As a kid, I would just start using everything with everything else, and the hints from failed interactions wouldn't clue me in. Now I see they make a really god job at telling you why things don't work and what you should try instead.
I was pleasantly surprised that my daughter thought the game was hilarious. I expected her to get bored quickly, but we played through it all together.
