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I can't tell whether he will be the boss if you take damage or not, but i do recommend trying to No Hit the Gauntlet fully, maybe it'll be more likely for him to appear.
For me, he didn't show up at all until I had completed the gauntlet about 20 times.
I suspect it had something to do with his dialogue; after talking to him often and exhausting all his dialogue (must choose same option multiple times to exhaust), the Caretaker asked me a question. After answering the question, he suddenly started showing up for me.
Hopefully this works for you too.
Happy to help!
Great! :)