Why are you disconnecting the shrouds when trailering? I just bungee them up by the mast and forward.
With the rudder pins... for like, $2 you can go to the crafts section of Wal-Mart and they have a baggie of 12" aluminum wires for making fake flowers & stuff. You can just push a bit of wire through the hole in the pin leaving maybe 1/2" out on either side. Then use pliers to bend the wire around so it's not poking anything important or hanging up. Later you can just un-bend the wire and remove & throw it away. The only reason you have something on that side of the pin is to keep it from falling out and losing your rudders in the unlikely event that you turtle. The wire doesn't carry any load.
