Yeah, it's just that the guy feeds off negativity, and he's also trying to get closer to Hell (via Alem), so effectively your proposals both... help him out :))))

He doesn't have the human empathy for self-doubt, he'd just metabolise that for power generation.

I'd go with annoying him with the creatures, maybe one-two? I'm not sure how Vanessa would know it worked, unfortunately, but happy to do that, if you want.