.Well, by that point Tayuya and Kiro would've inadvertently divulged enough information (through casual conversation, the entire reason Hinagiku put them together is so they'd talk and basically spill the beans of their own free will.) that their default soft stance would come into play and Tayuya would be classifed as 'helpless girl blinded by Orochimaru' much like many of the people Naruto Talk-no-Jutsu's and Kiro... would just be an overly vengeful child. At that point their rationale may be to simply leave him to his fate of being pusued by hunter-nin, as the leaf is practically his buffer, and he's not really a prisoner if you're protecting him.Plan is good (Not sure how it helps Kenji XD) but we need a reason the Leaf would let Tayuya & Kiro go with Sagiso, a foreigner when they are prisoners.