Round 2: It's hard to tell, because we need more factors, like if they know of each other's presences and they're skills. If this were true, it's pretty much a tie. Rambo is better with prep time, even a considerable Batman in this situation, but lacks the understanding of his environment that John holds. John has almost any connection in the city and with as much prep time as he needs, he could easily equip himself with almost anything. I'll edge this to John since he has more connections in New York. So John wins with high difficulty.
Bonus round: John wins with absolute ease. It couldn't be more blatantly more obvious.
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