"Our master Rabbi Chaim of blessed memory used to say that when there is one question in a passage, one gives one answer; for two questions, one gives two answers; but for three questions, one no longer gives three answers, rather one must give a single explanation, namely: ‘we are not learning the passage correctly.’ For the multiplicity of difficulties proves that something basic is not understood by us in the passage, and then further answers will not help; rather, one must learn the passage again from the beginning.

And he brought proof for this from what is stated in the Talmud, Chagigah 3b: ‘The Rabbis taught: Who is an imbecile? One who goes out alone at night, and sleeps in a cemetery, and tears his clothing…

It is always where he does these things in a deranged manner. As for sleeping in a cemetery, one might say he does it so that a spirit of impurity may rest upon him (= if he only sleeps in a cemetery, perhaps that is why he does it, and if so he is not an imbecile); as for going out alone at night, one might say anxiety has seized him (= he is worried, or hot, and therefore he is not necessarily an imbecile); and as for tearing his clothing, one might say he is deep in thought (= absorbed in thought and absentmindedly tore his clothing, and so he is not necessarily an imbecile). But once he did all of them, he is like one whose ox gored an ox, a donkey, and a camel, and it became established as dangerous for all.

So we see from the Talmud that the first and second time we offer an explanation for why he did it, but by the third time there is already no explanation. For instead of answering with three explanations, it is preferable to give one explanation: that this person must necessarily be fundamentally different from others — he is an imbecile.”

You can leave it as a single difficulty on the Talmud: why don’t we give three answers? (A difficulty based on reasoning), and let it rest unresolved. In the terms of the new columns, there is here an Anna Karenina probabilistic principle (the product of the probabilities of the answers no longer meets the threshold, or is lower than the probability that he is an imbecile), and therefore even with three answers all you really need to examine is the product of their plausibility against the plausibility of the single answer. That quickly brings us back into the warm embrace of triviality (that one should choose the more plausible position).

I completely agree. More than that, I’m convinced that if there really were a good/convincing but complex answer, every halakhic decisor would choose it. The same is true in science. But I don’t agree that this is trivial, because it still sheds light on our way of thinking. In particular, you can see this in a situation where you have no estimate of the plausibility of the answers. In such a case you would choose one and not three, and there it becomes a binding criterion and not something trivial.
By the way, there are similar criticisms of Ockham’s razor as a whole, that it is basically trivial: choose what seems more correct to us. There are also other criticisms, that it is a recipe for conservatism, etc.

Understood. As an aside, I’ll mention that when I heard this quoted in the name of Rabbi Chaim, I was immediately surprised why he bothered writing an entire book full of answers about Maimonides, instead of simply explaining with great ease that Maimonides was an imbecile (or was forced under threat of a dagger. And what about supervision over the text? We’ll answer that there was no supervision, and all the difficulties disappear at once).

Suddenly I noticed that the rule really does shed light on our way of thinking, but that illumination has nothing to do with Rabbi Chaim’s proof. Because in the Talmud we are dealing with completely real-world matters, and there is a perfectly reasonable estimate of how many people in the world are seized by anxiety, how many long for a spirit of impurity to rest upon them, how many are absentminded thinkers, how many have this and that, and also how many imbeciles there are. So the explanation there is only according to the probability of the product of probabilities. If so, the citation from the Talmud is merely an illustration for the torch that gives light, and not an example of light that broke forth from the torch along some particular dark path.