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Chip:

I think if he stayed under Price Chip would have a much stronger "survive survive survive" mentality and be much chiller with killing people

I think he would still be a goofball and a prankster, but Price seems to derive amusement from much meaner jokes so I think Chip's pranks would end up on the verge of cruel without him realizing it until he meets Jay and she gently coaxes him into joking in better taste

canon Chip is extremely attached to Arlin despite the fact that he didn't live with him for very long and hasn't seen him in a decade -- I think this is because he looked up to him so much and enjoyed his life and felt so safe while he was with him, and based on this assumption I think Chip would also be extremely attached to Price because he would have provided a similar situation of security for him

Chebo is loyal to a fault-- he absolutely refuses to give up on Arlin, he considers Lizzie family, he never gives up on helping somebody the albatrio have decided they're going to help, and he would run to the ends of the earth for Jay and Gil -- he has, too, we've seen it (Featherbrooke moment). All this to say I don't know if he would ever betray Price in this world. He might leave to help Edyn once he considers Jay one of his own, but I honestly think that unless Reuben did something monumentally fucked up to Chip specifically that he hadn't already been desensitized to, he could never hate Price and would run to the ends of the earth for him too

speaking of Arlin, having a stable family in Allport via Price's gang might have convinced him to grieve and get over his disappearance

I like the idea of him holding onto his memories of Arlin for comfort even if he has "gotten over it" and using the coin Arlin gave him often in magic tricks for kids he passes in the street, but also perhaps in some messed up slightly evil little trickster ways:

perhaps going on the quest to save Gil resurfaces his secret conviction that Arlin is out there and can be found 👀 :)

Jay:

if Jay stayed the course and finished training with RAFT, she would have stayed with Kira and I'm sure they would be close friends and allies including when Jay goes undercover under Price

perhaps when Jay sees the poor living conditions of people around Price and his folks in Allport she may realize that reforming the navy isn't going to be enough to fix things and she becomes uncertain that staying with RAFT through everything is truly what she wants to do

while I think she would be even more convinced of RAFT's corruption, I think she might be even more against a war on RAFT because she would know so many of the people intimately

and spending so much time on her goal of trying to avenge her sister's death, hearing that the undersea folks are becoming dangerous (which is true, but only because RAFT higher ups are provoking them in secret), plus strategic manipulation by... pretty much anyone, Jay could be secretly hellbent on Gil's death as revenge for Ava (a great reason to follow Edyn to him)

And maybe she doesn't attack Gil right away because there are witnesses and whatever else and she's been planning this for too long for it to go badly, but while she's plotting in the background they sort of become friends??

imagine an alternate Not Ferin Well -- maybe Jayson Ferin isn't there but maybe Edyn is. Maybe Gil, who has been secretly hoping that humans aren't all as evil as he thought they were and finally got the chance to be proven right, believes wholeheartedly that whatever Jay needs to do is what is right and he lays down the armor that she poured hours into enchanting and puts his arms out. And maybe Edyn is clawing at Jay begging her not to shoot her brother who she has worked so hard to get back. And maybe Jay takes a deep breath, thinks of Ava, and gets her revenge. And then immediately breaks down and collapses because this wasn't what she wanted at all. But she has been convincing herself that this would make everything right and she tells Chip none of it meant anything and he says he doesn't believe it and she heals Gil and they're okay. And maybe Jay decides that revenge isn't the way to go and Kira has RAFT so Jay will take another angle to help people from and hey, what if maybe they decide to become a real pirate crew? Yeah, I think that would be nice :)

Gil:

design extremely inspired by @wasyago please go devour all of their art it is so yummy and wonderful

I think he started off as friendly and optimistic towards humans, but ran into some bad folks (either by pure luck or by the orchestration of the Elders) and began to distrust them

probably prone to initiating duels, and probably prone to winning -- likely has a battle trophy collection at home

still loses his sword to Jayson Ferin when confronting him about why RAFT is encroaching on undersea territory lol, the Sword of Destiny finds him somehow

I think it would be very difficult for him to warm up to humans on his own at first, but if Edyn is with them and can tell him stories of all of the wonderful things humans have taught her and how wonderful the land is, I think he's much more likely to receive it.

And once he decides that Chip and Jay are his true friends, he trusts them with his life because they have proven to him they do have honor (even if Jay attempts to betray it when she reveals she's a traitor) -- throughout the time he's known them both have lost any residual scent of evil they might have had