RolfAndreassen comments on Rationality Quotes December 2012 - Less Wrong
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Although I would infer him to have already been aware of certain exceptions, e.g.:
If you and your opponent both know eachother to be skilled and masters of the way, then attempting the same tactic a third time becomes a different tactic; you are making an attack which your opponent would never expect you to try again.
It's a common failure mode of intermediate-level students of a competitive discipline to fall prey to the simplest tactics used by the weakest beginners, simply because they expect their opponent not to use said weak and simple tactics. For example, experienced chess players losing repeatedly to a complete beginner because they're used to playing against stronger and stronger opponents as they were gaining their experience. I've seen it happen often, and it's happened to me too.
ETA: I acknowledge that the example above isn't quite what is seen out there. What I had in mind was a one-off thing - of intermediate players, a "significant amount" (not the majority, but I'd guess "enough so that most experienced players have seen it happen more than once") go through a point at least once where they repeatedly lose against a player much less experienced than them, because of the reasons above. This second point is also debatable, but I think it's worth splitting and distinguishing between the two.
In context, this particular quote seems to be talking more about large-scale battles than individual duels. So, if you've already launched your cavalry at the enemy twice, and they were driven off in disarray each time, then another try is probably not going to work even if your enemy doesn't expect it.
I didn't see any discussion of strategy or leadership in the Book of the Five Rings.
I have, however, seen many cases in competitive gaming where correctly judging what my opponent was expecting me to do allowed me to counter them more effectively. There are a large number of meta-levels there, and operating two levels above your opponent is typically as bad as operating one level below them.
It appears to me that Musashi intends his principles to be applicable to either duel or battle. There are several illustrations that imply that he is not just talking about duels:
I suspect that 'flanks' might be a more idiomatic translation of that last. But at any rate it is clear that Musashi does not limit his advice to individual combat.