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Well actually, I didn't underestimate him, I'm just lining out his various conflicting desires. He clearly learned from his VR experiences that being Solo would not solve everything. To throw away what he has now in pursuit of his own selfish desires would make him no better than Oberon or Kayaba, and he doesn't want that.
The entire SAO story was one happy ending after another, so it's expected that he'll turn back before jumping off the cliff lol... though if it was I he would've jumped off the cliff and murder someone along the way muhahahahahahhahahahahahha
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