If you owned a hobie, I could understand your fustration with putting them on and off.
I needed a damn hammer to get my 17's rudder pins in and out. The Nacra's just clip in, takes less than a minute to put the whole system together. They always come off unless I'm just dragging it from the ramp back to the lot slip.
I have an 18 and don't have a problem removing/installing the pins by hand. I do have the one piece gudgeons but I don't know if that makes a difference.
Thats 'cause your rudder pins were lovingly crafted out of 316 stainless by me when I fitted the one piece gudgeons on that boat! Aluminum rudder pins are more prone to bending when the steering flops hard to one side - then making them difficult to remove.
All I did to make the pins was buy some standard size round stock from a hard ware store that carries stainless, cut them to length and drill holes in for the ring dings. I experimented with tubular stainless pins but they bent just as easily as the solid aluminum ones.
I'm in the rudders off school.