Considering how easily Lelouch screwed people even with his NORMAL wiles in canon, I can't wait for us to have a chance to sink our claws into people like Rolo and Mao. All those sad, troubled individuals could use a nice obsession and new Prince in their life.
Mao may be a bit difficult to deal with if he's obsessed with Lelouch. Obsession generally would have another Intimacy attached to it, like Love, Hate, or Lust, which would affect how Obsession is acted upon. We'd need to make Mao like us first. And even then, that has trouble with it - remember that his solution to getting C.C. on a plan and having her fit into the overhead compartment was to make her compact by cutting off her limbs with a chainsaw. Even so, we might stand a chance since Assumption of Mu will make it so he can't read our actual thoughts. (what he'll get I still don't know, but it won't be our thoughts) Also, it will depend on how Geass interacts with demons and other non-human creatures - if he can't read the minds of demons, then we can give him tons of new friends and make him not lonely.
Rolo we're also likely to have a harder time with. The canon path of Lelouch legitimately acting as his brother due to having his memories altered isn't happening, and that's what made Rolo so susceptible to Lelouch - he craved that real love and affection he'd been getting for months. A similar angle might work, but we'd for sure need to use a Charm of some kind to get our hooks into him.
....Can we send him deep undercover in some far away place and then forget about him?
My plan is to use him as a means to activate our Act of Villainy:
Lelouch: "Tamaki, I need you to spy on <random person> for the next few days."
Tamaki: "Sure, but..."
Lelouch: "Quickly, Tamaki, time is of the essence. I'm counting on you. Find anything out that you can. I can only trust you with this."
Tamaki: "Yes! Of course, I'll get right on it!" *leaves for bogus mission*
Lelouch: *loses Limit*
