I wouldn't even bother taking the rudders off for trailering.
Nick, you're right on. At least with the Hobie system this is a wives' tale. All you need to do is create some additional locking pressure to stabilize each rudder and keep any parts from moving, like a bungee to the rear pylon.
The paranoia around this reminds me of a story my Dad told me about post-war power boating. Up through the mid 50's eveyone removed their outboards for trailering and hauled them in the trunk, because the weight would surely crack your transom. Can you imagine two guys horseing a 4-cylinder o.b. motor into a '53 Buick? After building two boats (not varying from plans but just knowing what was there) my dad started trailering with the motor on the boat. Everyone was certain the motor and back half of the boat would end up in the road soon. He sold the boat 30 years later, still solid as a rock.
Trailered a gajillion miles in the eighties and never had a problem with gudgeons, castings or pins, MAKE SURE THEY'RE TIGHT.