That's interesting. Good on you for asking them. Some ideas from my dumb little sector of time & space:
Probability-minded theorists (contingency planner-directors) are routinely one of the smallest population groups when population is broken down into cognitive function or temperament. Theorists are already a comparatively small group in the first place.
Typical analyst-theorists don't naturally give conscious attention to the language of probability; for one it is cumulative and closed-ended (single point of arrival) rather than open-ended (possibility-focused).
Contingency planners don't generally run in academic circles due to the way they feel blocked by, and block, open-ended discussion.
Contingency planners themselves are more likely to communicate their favored perspective in terms that lend a guise of certainty; this may be related to the impactful way the visualized, singular outcome forms from a powerful visual image in the mind's eye (a distinct process from subvocalization for example). It may also be related to the naturally planning-repressive "who knows; how can you know that" effect of society's feedback to this function.
Society lacks language/pattern-custom to adequately follow up on probabilistic lines of thought when they are introduced in arguments.
Not everything that is plausible is true.