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Do you unlock different dialogues based on where you stand?

yes

Oh god... how many are there total? Does how high up you are matter?

"You gotta break a few eggs to start an egg breaking business."

there's 3 sets, so only 18 total. the "theme" of the environment so to speak corresponds with the dialogues you get. height doesn't matter

Could you put the dialogues up on some wiki, I don't want to replay the game 3 more times lol..