Well, maybe Matts right & there is a whole bunch of defective pins running around then.
I do apply marine grease on the rudder pin and on the molded in brass piece. I also spay lines and Twist & Stow mech with Silicone spray.
I know I'd be frustrated as he11 if I broke pins every few outings. 2 boats owned almost 30 months and only 1 broken pin between them. So, it is a real head scratcher and why I post my experiences.
I have been out in a wide & wild variety of water, even surfed with the island once - which I flipped sideways in a roller. But, normally I'm never out intentially in aything 20knts or over.
EDIT: Maybe this is IT! Both rudder pins on our Islands are the old plastic rods with cotter pins on top & bottom. They are of the "legacy" original design. I seem to recall Roadrunner mentioning that the older, solid pins were stronger. They would be harder to replace than the tapered "D" style pins - but, in my case at least, they sure last a long time.
Hope this helps.