At the 0:10 mark you can see in this new video that Skiff has to have his sail down in order to pass under the risers. I think if they just had made him with wheels (like Ucwepn says) instead of him up on a flat bed, they may have prevented this and the sail would have fit under. Just doesn't look right running around with his sail down or is this how he was in the movie/show?
https://www.youtube.com/watch?v=2u2hbYL3I7s
https://www.youtube.com/watch?v=2u2hbYL3I7s