Yes. The context that has to be taken into account includes the social context, ie. 'I am sitting in a room taking a test, I cannot request clarification of the question, the person who wrote this test may be far less intelligent than me, etc'.
By making an effort to choose the possible answer that I perceive as the most boring and conformist, rather than one I might find brilliant, funny, novel, and suggestive of further even more interesting ideas, I am pursuing a strategy of "favouring theories that match every other part of observable reality", as you put it.
Is there any reason that in this case and in the case of the parent comment, there's a tendency to jump to conclusions about the intelligence level of the test/puzzle writer? Do truly intelligent people never write lousy questions?
When I was young, I was furious at "Skip the first letter, keep every other letter, and what does it spell?" Data was something like "ghfeklmlto", and my answer was "hfeklmlto", of course.
By making an effort to choose the possible answer that I perceive as the most boring and conformist, rather than one I might find brilliant, funny, novel, and suggestive of further even more interesting ideas, I am pursuing a strategy of "favouring theories that match every other part of observable reality", as you put it.