Kevin,
I agree that you will get a variety of opinions on whether or not you should trailer your cat with the rudders on. I will say this from the viewpoint of being a Prindle 18 owner (1981 model). My boat has almost as many miles on it trailered as it does on the water. When I trailer the boat I strip it of everything that is nonessential or could pose a problem on the road, which includes rudders. Prindle rudders aren't the easiest things in the world to tune and to do it right you really need two people. I say, mark your cross bar adjustments when tuned with a grease pencil and do the same to your lock nuts (though they really should not come loose if adjusted correctly) and take the rudders off the boat when you are done sailing via pintle removal. The other thing I warn you about is that the casting on Prindles is notoriously weak...if it breaks it will break on the part that connects through the pintle to the upper gudgeon or along that line. Good luck

Matthew