Oh interesting! Yeah I'd be interested in something, I have a couple options to throw at you though.
One important question would be about dark siders vs sith. Cause I have Salis who WAS a sith but doesn't call herself one anymore, though she's very dark sided. Course, she never had a massive reputation as a sith either, and left before the Jen'ari ultimately fell apart. But I do have an alchemist who is also very dark sided...but again, not quite sith. Both of them would honestly pressure him to go further. Salis would actually be a little in the middle, her opinion is basically. "Do whatever brings you the most joy whatever that may be, though if it hurts me I'll make you suffer." while the alchemist/biologist (
Walker
) would pressure him only because he wanted to see him go further to the darkness. He'd probably even try to give him some little amount of help just to see what happens when someone who was jedi indulges themselves in the dark. Salis can hide her presence, while Vash is pretty much entirely incapable.
Another that could be used is
Shavara
, also an alchemist but far more light sided. She's younger than either of the others and far less combatively skilled, though fairly powerful. She wouldn't actually pressure him due to light or dark sides, but rather due to how it might be affecting him if she could see it. Far as Shavara knows, due to her culture, light and dark are just called 'way of thought' and 'way of emotion' (or heart, don't remember at the moment). Both are acceptable methods, but neither should be utterly given into. So she might press him to moderation, which may be utterly useless to him but would be something she could do.