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Re:The First 15 Years of PyPy – A Personal Retrospective by uryga on Sunday September 09, 2018 @09:42PM (#17948842)
I don't know about your question, but Cython recently added [1] the option to use native Python type annotations (Python 3.6, PEP 484) instead of its previous C-like dialect. That could lead to a situation where a sensibly type-annotated Cython file can still be a valid Python file – that would help with portability.

[1] https://github.com/cython/cython/issues/1672#issuecomment-33...

Re:The First 15 Years of PyPy – A Personal Retrospective by acemarke on Monday September 10, 2018 @11:17AM (#17952407)
Cython also supports writing type annotations in a separate .pxd file. It's a bit awkward because you're effectively duplicating all function + variable declarations, but it _is_ a valid way to keep the original Python source intact.

(On a side note, using this feature led to a particularly memorable debugging session that set a personal record in terms of time spent vs amount of code changed to fix the issue: https://news.ycombinator.com/item?id=11115110 ).