There seems to be some interest in making this an SSS event, so I looked into it further.

One rule (yes, there are rules) was apparently added after the race in the video. The boat and trailer must be at least as long as the vehicle towing them. Since I drive a Honda Insight and own a 38' Alerion, this shouldn't be a problem.

Another pesky rule is that at least three feet of the boat must still be connected to the trailer at the end of the race. It doesn't say which three feet.