These raven interactions are all intended. How it works is that everything that happened simultaneously are considered the same effect. Therefore initiate + emissary will only proc raven once, while Initiate + obelisk will proc raven twice. Huntress and lightkeeper follows the same rule. I made it this way so that trigger effects will be easier to balance and for player to predict, but I guess if this rule turns out to be unintuitive for too many people, the alternative will be to have them based on numeric value (like deal 2 random damage for each point of faith gained)
I agree with the comments on endless mode. My intention is not to just brick some builds completely, but rather that player will need to identify and mitigate the weakness of their build rather than keep using the same strategy. It is probably a good idea to have some endless mode exclusive mobs with weaker version of those hunt mechanics.