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When an engineer says something is “non-trivial,” it’s the equivalent of an airline pilot calmly telling you that you might encounter “just a bit of turbulence” as he flies you into a cat 5 hurricane.
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Ideally, I'd hire the great Python programmer and have them pair-program with a competent Java developer. The Java developer could provide expertise on concrete things like the minutiae of the Collections classes, and the probably-frequent-at-first "no, in Java you do it this way", moments. The Python nerd could chip in with "what about this case?" and "why don't you do it this way?", and the whole would be greater than the sum of its parts.