Feel free to ignore if you don’t wanna answer, I just wanted to pitch something to you, since I’ve seen you briefly-kinda talk about it in the past:
Say Andrea Kormos wasn’t killed by Dean, and say Benny didn’t leave her on Prentiss Island—very canon divergent lmao—; Do you think the two of them would continue running their maker’s operations together, or would Benny somehow convince her to leave that life behind and choose a different kind of freedom? (The second one implying that Benny would put in the work and effort to show Andrea a different way of life).
This is probably more fanon than anything, so I apologize; you just usually have great ideas, so I thought I’d bounce them off of you and see what you thought. ❤️!!
Oh, no. I don't mind!
Hmm, not sure how I feel about Benny being the one to show Andrea the correct and ethical way to be a vampire, when she's the thing that Benny oriented his morality around originally... Is Benny really going to show her a different way, when the different way was originally... just HER?
I mean. Maybe. But it doesn't feel quite right to me somehow. Benny doesn't imho LOOK much like a monster character that builds community or even rebels against the way of doing things per se. Or at least not naturally (and that's ok!) He usually runs, then later gets Revenge. He's more Mary Winchester runaway than, for example, Garth's father-in-law, Rev Jim Myers. (SEE: Jim Myers, who challenged a whole werewolf Apocalyptic belief system and built a community.)
This is a BIT of a departure from your original question:
Andrea
I think a more interesting story would be Andrea coming into contact with something, or someone that made her re-evaluate humanity on her own terms, or even remember her Greek roots.
It would hurt, probably, for Andrea to rediscover what she loves in something outside of Benny, but I think that's how it might go on the high seas unless Benny grows in a very specific way.
Benny borrowed her humanity, and then when she fell form it, he was completely fatalistic and dehumanizing to her. Especially after Purgatory, he's not a vampire who's inspiring people to "new, ethical ways." -> ("We're all damned.") I can't imagine him carrying that mentality on the high seas with any success. I think she'd have to find this way on her own, free from the father vampire. I think Andrea's arc should go in an opposite way of Benny's suicide: "I remember who I am now: I want to support people DESPITE being a vampire."
Benny died because of how he felt about his own plight: "I don't fit, so I might as well do something good in pursuit of my own preferred suicide/fatalism/hopelessness."
Andrea's heroic putting-her-life-on-the-line would in my mind need to be the opposite: "I AM still like you; it's my mutual humanity with you that makes me care enough to give my own life for something I discovered I still care about."
That's what we see at the end of season 10 with corrupted Dean:
DEAN: And you know what? I don't blame Rose [for her own corruption] anymore.
&
DEAN: I let Rudy die. How was that not evil? I know what I am, Sam. But who were you when you --when you drove that man to sell his soul... Or when you bullied Charlie into getting herself killed? And to what end? A-a good end? A just end? To remove the Mark no matter what the consequences? Sam, how is that not evil? I have this thing on my arm, and you're willing to let the Darkness into the world.
Dean's struggle with his own monstrosity let him see humanity in himself, albeit an ugly humanity. And monstrosity within humanity, for that matter.
OFC, due to the psychological damage of 24-7/360-war grayscale Poughkeepsie Pure (TM) Purgatory-world, Dean and Benny were the opposite of this headspace when they killed her, so EYE think it'd be THE natural way to handle her arc. I believe SHE is the NARRATIVE GHOST haunting The Werther Project ep too in a major, MAJOR thematic way on this issue specifically.
ANDREA: I'm RIGHT here. I'm [still] here!
(Why can't you see me?)
///
Benny
You know, originally when I watched, I thought maybe Benny consensually drained Andrea when living away from his vampire nest, but on second watch, he's emphatic that in that time with Andrea, he used the black market, which is interesting. The ethics of the black market is a very Sam Winchester-coded approach, like. I mean. At minimum, it's a complicated, tenuous sort of ethics, right?
Black markets can and IRL do get utilized humanely for food, medicine, or other necessities. BUT. It CAN lurch into, "I don't condone it, but my support comes in ways that enable others to be exploited, but don't make me personally feel guilty." (Which again, what are the alternatives? I don't know. It's certainly a problem I'm very sympathetic to.)
Aside/// This could also be a smokescreen for using Andrea ofc, but again, why not just say ethical rather than black market specifically? So he's either lying, AFRAID to drink Andrea (an anon pointed out that almost all drinking results in kills a la Dean and almost-Lisa, so it's something he wouldn't dare risk), or Andrea having big juicy objections about the practice of it.
All interesting in their own right.
But to the real point: even if Benny did use the black market or rely on Andrea, I'm not convinced he's ever in a position to have "put in the work" to "show her a new way," even out on the high seas. He can't even talk to a vampiric Andrea without passive-aggressively calling her a whore (yes, as a ruse, of course), then immediately spiraling when she expresses fear and hopelessness—calling her a non-person and a failure he wants to leave in a smoking crater.
This is not a charismatic guy. He's not the kind of person who's going to convince Andrea of anything. More importantly, he's not the kind of person who's going to convince ANYONE of anything, because, crucially, he doesn't actually believe in anything. Which, again, tragic and very VERY understandable to be beaten down like that.
He sees "something" in humanity, but that seems, esp without Andrea, a tragic way to make himself more palatable to his troubled idea of himself. (Fatalism.)
On his second-go-round at life, it's obvious he hadn't planned much beyond getting his Big Revenge. (A la John.) What on earth is he going to teach a high-seas Andrea that she doesn't already know? "Get lucky and take a human lover as supply? Pick off rich people yachts and heiresses or Evil People who 'deserve' it?" Maybe she was already planning to "pick up where Dad left off," but have it be about "Saving People, Drinking Things" approach.
But it's implied in the deleted scene that without his one friend helping him, Benny fell off the wagon and fed. That's pretty heavy, and again, it doesn't speak to a resourceful vampire who has anything to teach Andrea about how to make it work. While it IS true Sam IS working behind the scenes to keep Benny branded as outsider and keep people hot on his tail, Benny's OWN past is also doing that in equal measure.
In canon, he goes to his granddaughter to get support from her, not really to give it. ("I even found someone to hold myself accountable to. Best kind of someone, Dean. Family.") And it's hard to be a source of support when you're unstable yourself—hence the ghost-of-John energy. And the Sam-coded, "I don't trust myself," of it all. Could he have grown past that? Sure. Cas did with Claire. But Benny's situation is different. After his pragmatic acts of loyalty are over, he's searching for an ephemeral "goodness," and I think that's a much more significant barrier to overcome. He's not even looking for redemption or ways to support others, really. It's just not on his radar.
Benny really is THE vampire. He's like Sam in that he's so busy surviving he's not thinking much about others much except if it aligns with his immediate goals. Helping Dean to go topside to get the big Revenge (talking sassily down to Dean about eating "the little piggies" when Dean pressed him about safety), saving Cas to ensure Dean's trust, going his granddaughther he's apparently never had need of visiting before, and then helping save Sam again because he wants really the big S Suicide.
BENNY: He's chasing a memory, Dean. That's all.
He might as well be talking about himself.
EDIT: I've said this before but Benny DOES remind me of if late-season Mary was faced with the Hunter John, who descended from the Goodness of Civilian Life into the Corruption of Hunter Life and Became Too Much like all the ugly things Mary saw in herself. But I think Mary IS more like Dean on the whole, in that she's pro-Redemption, because despite the odds, she still believes in it for herself (which is what imho The Werther Project really shows)!