I got the impression from the photos I saw (I can't find them now- don't remember where I saw them?) that the rudder pin on Shazza bent first, and then levered its way out of the holes in the transom and rudder gudgeons. If that's the case, then as Josh says the best remedy is to ensure the pin is loaded more than once at the top and bottom, in "double shear" in engineer-speak. So using two bottom transom gudgeons, with the bottom rudder gudgeon between them, means the pin needs to bend twice to handle the same load AND those bends are acting in opposite directions so the rudder doesn't displace upward and increase the leverage and increase the pin load, etc. Never allow any significant gap to occur between the transom and rudder gudgeon sets- that gap is the lever acting to bend the pin, rather than load it more purely in shear.
ShazzasGudgeon.jpg
So with the hardware in this pic, I'd capture the lower transom gudgeon lug with two straps on the rudder, or use a beefy strap on the rudder at the bottom, and capture it with a second lug above the rudder's lower strap.
Here's the output of a spreadsheet I put together for another project, then adapted for the i550. It doesn't design your whole rudder for you, but it gives a pretty good idea of how the loads work.
Rudder design.pdf
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