"Understanding the ambiguity" is fine if we are talking about trying to figure out what was intended by the people who put the ambiguous phrases in. But the issue isn't about who can "understand" the ambiguity, it's about who's going to be making things up and giving the ambiguity as an excuse. Asking whether bureaucrats or judges are better at "understanding the ambiguity" is the wrong question--understanding something and doing it are very different things. They'd just understand that the law is supposed to be X, and give a spurious justification about it being Y instead anyway.
Your use of phrases like "thought-terminating cliche" makes you sound like a rationalist. In which case I hope you know what a quokka is. (For the uninitiated, a quokka is an animal that can't understand that someone might want to hurt it.) If someone has an agenda that is against your interests, having "better knowledge" and being "better suited to understand" and "having experience" just makes it easier for them to harm you.
