YES, Cas is the researcher. I envision Anna walking barefoot around the motel room in her tank top and jeans being kind of messy, and Cas gets kind of ticked off at her not messy and tells her to pick up after herself, but she just kind of ruffles his hair and is like, "Aww, you're so cute."

Maybe the second temptation is just gonna have to be quite loose here. If the bottom line is "don't tempt fate" or "don't test god", then the problem here is that Sam thinks god and fate are kind of bullshit to begin with. "Don't abuse other people's willingness to do things for you" is probably more doable. Maybe Cas and some people are gonna sacrifice themselves, but Sam says, "no way, this isn't how it's gonna go down." I can't help but think Cas should die in the first temptation, but demons can't possess angels, no? Bobby should be the second temptation if only because Sam cares more about him than he does about Cas.