'I need to meet with 5 of them before I make my next move.'
Azrail in his heart already has an idea of which side he wants to join, but before that, he needs to drive the market price in. DeathMark needs to put in and show his place and talent to make it such that Azrail will receive better offers when he wants to join any faction.
'Gotta be careful on how I move this.'
None of them are idiots or useless ones. Once Azrail joins, he needs to lay low till he gets the full picture. Be it the lowest sect or even this humongous organization in front of Azrail, all of them will have at least one small weak leg for him to break, which will create the domino effect that Azrail wants to, he would be more in sight then.
