Those rules questions were just too easy, since they were simply test
questions where the answer could be looked up. Even so, they proved too
difficult for some.

Here are real life questions from an actual event:

A ship "A" is leaving harbor by the main channel. As A nears the mouth,
he sees ship B outside the channel to his right, apparently intending to
turn and enter the channel. Question 1: should this be considered a
Crossing situation, since the boats are in that orientation; a Passing
situation, since they seemed destined to "pass", or is it Narrow Channel
situation, because vessel B is about to cross the "extension" of the
channel?

The situation evolves: Vessel A is intending to turn left when leaving
the channel. As he approaches the end of the channel he sounds two
blasts, proposing a departure from the rules to pass starboard to
starboard. Vessel B has squared up to enter the channel and responds
with two blasts. Both vessels turn left but the maneuver was started
too late and the vessels collide. Question 2: How do the courts assess
blame?

Credits for the description of the event when I give the answer. No
fair posting if you're familiar with the case.