That seems like a repeating cycle though: PC has to do nice things before of personality gate, gets bonus to nice personality.
Nah, the personality is dynamic anyway. I would avoid gating it to personality if you are planning on doing a personality change in the end--and the same in reverse; I would avoid using personality changes if you are going to gate the content behind personality. Choosing one over the other is probably better than doing both at the same time.
Two separate events might be worthwhile, especially if the main one has a major tone-shift reveal. If the later repeatable event's tone is spoiled due to the reason that they all wanna bang anyway, you can make the situation more playful and exaggerated than the first encounter--so Steele won't seem so out of character if choosing to pursue in the saving. So at first, it may seem like a tense situation, but later becomes a "catch me if you can" kind of thing.