If yes, until what number of tails could he go up against?
Remember, we are talking about 100% Pain, not the one who fought Naruto. That Pain had just destroyed a village, he was at less than half his chakra at that time, or so we can presume.
Remember, we are talking about 100% Pain, not the one who fought Naruto. That Pain had just destroyed a village, he was at less than half his chakra at that time, or so we can presume.