A Synthetic Theory Of Monitoring: http://t.co/omCnqcfQqd Effectively choosing, collecting and viewing the right metrics is hard.
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Choosing the right amount of content to put on each docs page is surprisingly hard.
I've seen info/man pages as a single large HTML page and it eventually slows down the browser. A short page with a short scrollbar is less intimidating and you're more likely to read to the end.
Choosing a syntax for a new programming language is hard. You want to be similar enough to an established language to avoid scaring off users.
You still want to be sufficiently novel to be recognisable. Which languages do this well?
Difftastic is effectively computing the "tree edit distance" between two ASTs, and there's a bunch of papers on this topic. Literature review is hard though: sometimes a paper takes a while to digest, only to realise that they're solving a slightly different problem.