Nifty Emacs package of the day: speed-of-thought: https://github.com/Malabarba/speed-of-thought-lisp Provides brilliant commands for inserting parens and adding defns.
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I've started adding some --dump-syntax flags to difftastic to save me inserting random print statements when I debug.
I have no good intuition for when I should start adding debugging features. It's easy to do it too late in development.