Pretty much A.
I lack the information on when their relationship started to judge this fully. I know they got married after Steph lost around the time of the I Quit match.
He was already a 4 time champion by 2000. I think it helped him stay on top for as long as he did. He's an easy target for joking because of what he did. I don't he ever saw it like "I'm dating the Boss's daughter things are going to go great for me" I'm sure he saw it as "I'm dating Vince McMahon's Daughter if I fuck this up he's gonna kill me."
I would have done it in the same fashion except I probably would have ended my previous relationship before starting things. That's the only thing Triple H did wrong. He cheated on Chyna behind her back dating Stephanie.
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