Yeah, the helping thing was no doubt carefully evaluated, and may even have been another anticipated element of the testing!
Is Jake running from his father, or just from himself? Sounds like typical human male behavior at that age.
Obviously, the writers didn't have a clue at this point about what to ultimately do with the interrogation plotline. But they apparently did assume that it was a "double bluff" of some sort - that is, a plotline would soon be written where a conspiracy within Starfleet was to be an issue, and despite being painted in positive colors here, even the two people involved in fighting the conspiracy could not be trusted.
Perhaps Remmick was to be a baddie all along? It was a nice twist when he applied for service aboard the E-D; in the originally intended version of "Conspiracy" (with Maquis rather than bug creatures), perhaps he would indeed have begun serving, and would have turned out to be a bad apple?