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I would guess that squaring the rudder provides more rudder surface "further down" which keeps the rudder effective when heeled. First time I sailed a Laser28 and it was hard over, you could feel the rudder loss and the boat would round right up because of it.
Still guessing--if you were already "keel deep" with a rounded rudder, you wouldn't want to make it any deeper (unless you worked at Beneteau, ahem) so your choice would be to square it up, or extend it further aft (more expensive to start with).
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