I liked this post, I pretty much knew the why of it, but it was still a fun read. Sometimes complicated is not to hard. One other side benefit of cylindrical shape is the wind effect, not just the wind as it travels the road, but because of the shape the side blast of wind move more easily around it instead of right against it, so less chance of the wind causing the trailer to flip onto it's side.
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Yes, I think so too. The cylindrical shape will have an aerodynamic effect. If you take a look here you'd notice that the rectangular box has the highest drag coefficient.