Moon's all-out warfare could result in Jiro not really getting into his groove and faltering how he did vs Kim, but I think Jiro's smoother, faster, more refined offense is what makes the difference in a war. He'd also have the defensive advantage, which over twelve/fifteen, would add up. Although if Moon was just too brutal and has too much retard strength, it wouldn't surprise me. The sandbag power he had would certainly be more eye-catching as it lands on the less durable Jiro than the sharp combos that Jiro would land on the granite Moon.
Jiro at his best takes it imo. If Khoakor and Bueno (when Moon was admittedly not at his best) and even Richardson at points can exploit Moon as a technician, I think Jiro would too. Jiro wasn't so small for the weight either (he was a big cutter) and I wouldn't call him fragile either. I think Moon's sturdiness, though obviously exceptional, is slightly exaggerated. After an absolute sensational start from Moon I see Watanabe taking command with his right hook and taking a decision.
I think the Richardson fight, though technically a win, showcases quite a few flaws of Moon. For comparison, when Richardson was much more experienced at a weight only technically 3lbs heavier, Tatsuyoshi hunted him down much more efficiently than Moon ever did. I'm still really big on Moon, but recently have come to a conclusion that he is indeed slightly overrated.