I'm posting a response even though it's too little, too late, as I've nothing better to do at the present. In terms of your question:
Likely neither does he (know what it/they mean).
To me it reads like a variation on Dr.Udellís PIES questions. In other words, IMPO, to avoid copyright the above was construed. Consequently, to me, individual words on their own without explanation - make little sense and are therefore ambiguous in the extreme.
He's likely assigned each answer a numerical value, say 1-5. If in his opinion your answer makes sense to him, he assigns it a 4 or 5. Single words such as "Legality" are so broad and ambiguous to be laughable as there is no "right" answer since one doesn't know what the heck he is asking. Duhhh?