Tornado sailors (and A-Cat sailors) would probably never dream of leaving rudders ON for trailering.

Rick and I are weekend warriors. And we would never dream of taking our rudders OFF for trailering. We also do not disconnect sidestays or anything else that we can avoid disconnecting for trailering.

Kind of depends on how much of a "purist" you are, I guess. Our boats have traveled many thousands of miles with their rudders on, with no bad effects that we have ever seen.