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For me, worst case would be having a broken body because of falling but still alive. Where the only thing left to do is to bleed out slowly.
Used to play that mobile game a lot. Forgot the name though.
"The Melancholy of Haruhi Suzumiya" I believe.
Yes.
And if there's no hole, someone will make one.
Pretty sure it was implied that he did in the WN.
Imagine summoning Astolfo or any other trap characters to become the waiter/waitress in his shop.