gree,
There is more than one opinion about taking rudders off for trailering. Rick and I have traveled tens of thousands of miles without taking our rudders off, and never had a problem.

I'm not suggesting that you leave your rudders on, because sure as I do, you WILL have a problem. However, we like our rigging/derigging time to be as fast and easy as possible.

Some people are perfectionists and really enjoy the time spent rigging and working on their boats. Others just want to get to the water and sail. So I think that whether or not to remove your rudders is more a matter of philosophy than necessity. (May be different for the newer, super-lightweight boats.)