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I almost never see this construction in classical prose. (In fact, I'll venture I've never seen it.) However, it's in two of my favorite poems.

In this one, it's from the poem "晨詣超師院讀禪經" by 柳宗元:

遺言冀可冥， 繕性何由熟？

The other one is from a poem, by Li Bai if I recall correctly:

西飛精衛鳥，東海何由填

What does X何由Y mean?

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in classic Chinese, 何由 is the inverse form of 由何, and it should be in the inverse form ,however, you can understand it by understanding 由何.

何 what

由 [preposition] 1. from 2.because of 3.by(method, means,way)

so 由何 could mean, from what, because of what, by what. I guess, you would less commonly(Ok, at least I would) say,"By what, did you arrive at this conclusion?", instead, you would say,"how did you arrive at this conclusion?" ;furthermore, when you say "how did you arrive at this conclusion?", you would probably mean "It's impossible to arrive at this conclusion. I don't believe it", depending on the context. This also happens to 何由.

In your examples,I think 何由 means "how could".

By the way, I think this word is not rarely used in classic Chinese, I can give you another example from a poem 《茅屋为秋风所破歌》 by the great poet 杜甫, which was picked into the textbook when I was a student.

长夜沾湿何由彻 How could I bear the bad situation(the house is broken and it rains heavily) in the long night , until the dawn comes.

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  • oh thanks. by the way, i meant rare in old prose, not rare in classical as a whole.
    – magnetar
    Commented Dec 27, 2011 at 14:04
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    It is less common(but not rare), because a similar word 何以 will be used, I think. I could only come up with one example that is not from a poem, from 《孟子·梁惠王上》,"何由知吾可也"(how could you know I am capable?)
    – Huang
    Commented Dec 27, 2011 at 14:52
  • @magnetar I am a little curious, just curious. Are you learning classic Chinese?
    – Huang
    Commented Dec 27, 2011 at 14:59
  • more or less. I have read a lot of classical-Chinese stuff in English (Laozi, Zhuangzi, Han Feizi, Kongzi, Mengzi, 300 Tang Poems, Book of Odes, Book of Documents, some of the Romance of the Three Kingdoms) and usually study the books I like in Chinese after vetting them in English, but studying formally, no, I'm entirely self-taught. Classical Chinese is simply my preferred way to learn. I've found that I can read 50% of modern Mandarin newspapers even though I have never studied Mandarin grammar, just based on classical and what I picked up while living in China for a year.
    – magnetar
    Commented Dec 27, 2011 at 16:16

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