It suddenly occurred to Castiel that rain for a man like Cole was a likely death sentence for him and anyone who was around him. It was hard to discern just how this human had managed to survive with his condition, but then again, if they didn't press themselves to the point of impossibility, Cas would not have been willing to potentially destroy himself to take care of them.
"It is a good home," he agreed. "I...recall a place similar to this in my own world. It was not a rooftop, however the sentiment was the same."
He turned to face Cole, staring at him analytically. He would need to feel the soul itself to know for certain, but from what he could see, Cas sensed that the conflict within Cole's soul originated from always having to make a decision that was uncomfortable either way. As always, freedom of choice and its length of rope was apparent.