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Regarding endings that aren't in the game yet, I think the dialogue of the guy in the cave seems unfinished. If I skip-jump while having double jump, my character wants to help but simply can't. After tossing the stone, the caveman seems to forget I visited him before and I can't give him any of my jump powerups, even though I can give my multi-jump to the dog. However, I have no idea what could happen if I helped the caveman get out.

You're absolutely right. The character itself is, aside from giving some exposition and providing a gag ending, rather useless. I like the idea to build upon the "giving away power ups" idea to help him out. If only I had more time on my hand :D

perhaps helping him out could lead to you both waking up together? sort of like E+