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In game sense it just there to spice up the dps mechanic
In lore sense I think it just the way yoshi see how monk/martial artist move like in those action movie and like, unlike boxing they dont stand in front of enemy most of the time, they dance around sommersault, backflipping, attacking from any direction, thus the abundant skill using flank and rear position
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There are a lot of elements that don't necessarily "make sense", but for what it's worth, OP, the positional nature of monk is the main reason I didn't continue with my monk. It doesn't feel very heroic or monkish to be constantly punching someone in the back of the head. That's not what I think of when I think of a monk or martial artist, at all.