Alright, so one of the biggest questions is: can Dregn go CR? He is an character from the future going back in time. What would his death mean to the story? Theorizing around time travel is hard, because there are so many 'ifs'. Let's assume he can die, because he is born in the future, so it would be his future self dying in the past, no problems here. Him dying in the past doesn't mean him not exisiting in the future, since there is only one of him and history of his existance is not complicated.
This may be going too deep into a lore that is pretty shallow, but hey, speak your mind, maybe we can come up with some clever ideas