While Mr. Morris's opinion is interesting and contains some good general advice, it is far from law or common practice to have dedicated look-out with no other duties on private recreational vessels. Anybody who sails alone violates the letter and spirit of this excerpt, as no sailing boat has an all around view from the steering position.
Is it your opinion that sailing alone is always a violation of Rule 5?
Back on topic:
If you get stuck out at night without proper lighting, due to equipment failure, loss of wind, whatever, with or without stupidity involved. You are now a danger to yourself and others, find away to be seen and get to the nearest shore.
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