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I think you would need to take a look at the character's powers and their effects, and then utilize that into the skill challenge somehow. Say if an effect is that they can move the creature one square, they move the creature into flanking for another character giving that character a +2 bonus...

Hey, I would love to implement a system like this. One thing you would have to think about though, is encounter and daily's. Would encounter simply give maybe a +2 more then an at-will, or would an encounter success count as two successful skill checks? And a daily? I'm just throwing questions...