I've always tried to look at programming in a similar manner as writing research papers, your ideas are no good if no one understands how they're put to paper. Explicitly stating your intentions is better than assuming the reader knows the subject matter. If something is clever, overly-compact or your reviewer expresses confusion, rewrite it or at least spend an extra line or two in explanation.
At the language level, I miss Perl's handling of regexps and shell commands (which consist of large amounts of this codebase). Python requires a fair amount of overhead to handle both and always feels a little clunky. While I'm far more fluent in Python, I typically reach for Perl when needing to quickly handle log files, automate shell tasks, and prototype ideas. On the flip side, now that Python supports type hinting, function signatures are much more valuable, and overall I feel I can write far more robust tests in Python than Perl. Given that the direction of the project is to move from a collection of one-off scripts that just kept on growing to a tested, maintainable, modular codebase, Python is the better choice.