I was amazed that I cared about Rowena's death. Wait, that sounds heartless. But she was a character I absolutely detested when she shared screen time with Crowley. On her own, she blossomed, and her friendship and working relationship with Sam was a delight. And it's clear she prefers older men like Ketch or Gabriel; the Sam comments are just mild flirting. This last episode hit me really hard because as I was watching it, I thought about the fact that in many ways, kind of like Jody, Rowena became as much a mother to Sam as his own mom was, maybe more so because she didn't spend most of her time off hunting with an enemy. (And there's an incredibly fucked up parallel running through both of the surrogate mom figures - he (re)killed Jody's son because she couldn't, and Rowena asked him to kill hers. No wonder Sam gave up on wanting a normal family life.)

I might be forgetting things, but... It feels like the first truly major time where the brother's roles are switched. Sam's always asked to kill himself so that his allies and loved ones live (he even killed his broken selves in S6; he did have to send John back in S14, but that's not really killing him). Dean's the one who's asked to kill his allies for the sake of the greater good (Sam, Benny, Sam again, Amara-ish, Jack). This is the first time where Sam's had to kill someone that truly matters to him (he tried to kill Castiel, but that was more defending Dean IIRC). And it's a mother figure/mentor, too. His mom died trying to protect him, and now here's Rowena calling him dearie, telling him she believes in him, and dying for him.

It's a little fucked, and I feel for Sam, is all I'm saying. And Rowena died like a boss.