Isn't it funny how we can read something and what we bring into the headspace drastically flips our impression of it? Never ceases to amaze me, even though we see it acted out in fandom religiously! Nodding back to your chalice/sword post (which I loved loved loved!), I think Dean falls into the role of weapon instinctively, which is why I threw a lot of 'blades' and a 'Dean' into his trail of thoughts; it's almost a place of comfort for him. Hopefully, Sam can get him to see differently, or better yet, he can come to that place on his own volition!