I love that Crowley is just so good at his job. His new and improved Hell waiting line is awesome. I like it that he's realistic about his chances when it comes to Sam and Dean.

Yes, this is why I think he's one of the more compelling villains so far.

He didn't go hang out with Dean while he was at Lisa's and Dean has never done well with being left behind by family. Cas wasn't able to help with Sam's soul either and he knew about Sam being back and he didn't tell Dean. Everything going on hits a lot of buttons for Dean that have him verbally lashing out. He's not a great communicator to begin with and add a layer of hurt on that and it's even worse. I also don't think he believed Cas could go that far off the reservation. When Dean finally saw that Cas was making some truly awful choices, he tried pretty hard to soften his approach and remind Cas about family ties, which for Dean are a prime motivator.

YES, I agree with all of this.

Hope you enjoy your sleep!