This is a clever little exchange, and I'm generally all about munchkinry as a rationalist's tool. But as a lawyer, this specific example bothers me because it relies on and reinforces a common misunderstanding about law -- the idea that courts interpret legal documents by giving words a strict or literal meaning, rather than their ordinary meaning. The maxim that "all text must be interpreted in context" is so widespread in the law as to be a cliche, but law in fiction rarely acknowledges this concept.

So in the example above, courts would never say "well, you did 'attend' this school on one occasion, and the law doesn't say you have to 'attend' more than once, so yeah, you're off the hook." They would say "sorry, but the clear meaning of 'attend school' in this context is 'regular attendance,' because everyone who isn't specifically trying to munchkin the system understands that these words refer to that concept." Lawyers and judges actually understand the notion of words not having fixed meanings better than is generally understood.