This just now hit me, but I now feel sure I know what's going on with "Jean."
The key was in how hard he tries to talk you into a relationship with Asterion.
We know he voted against Athena's plan. We know he wants to free Asterion completely. And we know he's behind the Argoi, and therefore chose the pseudonym 'Argos' for them, deliberately. And in his attempt at killing Nikos and then Pedro, he doesn't lose control and slip into recursion until AFTER you interrupt his attempt to kill Nikos. The killing of Nikos, of Argos, then, is intentional, and part of the plan. Which must mean that his use of recursion is intentional: presumably, by bringing to bear enough recursion on the labyrinth, he hoped he could override the story with a different one, one in which he wins, and one in which the person in the Io role is released from captivity.
To do that he has to cast as many roles as possible. Io is easy, Asterion's already a cow in captivity. Hermes disguised as a mortal is easy, too, that's his role already. Argos needed time and an opportunity, but when he saw one with the establishment of the hotel, he took it, and put his own agents into the system. Their actual instructions are irrelevant. It didn't matter, to Hermes, whether any individual Argos succeeded or failed, he just needed them to be "a captor" and "called Argos."
So why act NOW? Why during your tenure and not Clement's or Jean Marie's? Why, when Nikos returns to the hotel, does he say that Hermes has suddenly decided to take action? What does that have to do with his nosiness about your and Asterion's relationship?
Because he thinks the final role is finally cast. A Master, a Supreme Lord according to the laws of the Olympians, who is IN LOVE with the Io.
Hermes needed to a wait for an MC who could play Zeus's role.