The Python IAQ: Infrequently Answered Questions
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The document says it was written shortly before Python 2.5, which came out in September 2006. So it's probably about 9 years old.
Raymond Hettinger's PyCon 2015 talk "Beyond PEP 8 -- Best practices for beautiful intelligible code" has an excellent example of a Java -> Python case: https://www.youtube.com/watch?v=wf-BqAjZb8M
I thought most of the answers were quite prescient of features that would be introduced to the standard library some years later.