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Someone as "average" as your character seems a questionable choice for deep-insertion training. I'd imagine he'd come out as nothing but the most bland of technical sentries, which he's clearly not.
How did he manage to avoid the eyes of officers looking to kick the asses of people better than they were letting on?
Because he didn't do worse than most of his class. He did just about the middle. Thus, those officers were busy kicking the asses of the people below him, rather than him. He *is* the average, in a sense. so if the rest of the group improves, so would he, just to keep it that way.