You don't HAVE to... but you can if you want. Yes, he's supposed to be but really doesn't have to be. I just assumed he'd want to because he wanted to join her the last time she went in front of the council after a mission.
I said I think I'm not sure but I was the one who told him he should make a Spec Ops team so i assume so but I'm not entirely sure and I won't be saying so IC to get an advantage until i am entirely sure.
In regards to the council thread, because they haven't looked at it, if you want to activate it in that thread, go ahead. If you do/when you do, you can determine what's on the holocron. It's supposed to be a sith weapon of sorts, but I don't know/care the specifics beyond that. The fallen Jedi they had encountered was massing a collection of saber crystals if that gives you any ideas.