How am I reading this as a reflection of the relationship between Dean and John as well?
That's what I meant. I think she'll allow herself a degree of frivolity more than Dean because Samuel didn't raise her, but I think once she aligned herself with Samuel, she... trusted him more than she thought she would. And when Gwen gets angry at him, it hurts Samuel more than he thought it would. I want Gwen to join Dean and Gwen, I want that so baddddd.

I think the corollary with Crowley is with a lot of rich businessman who are all about the bottom line X)))) whether in this economic climate or not. So I'm simplifying even further than you are, ahaha. XD