Something else I think about a lot when it comes to Jill and romance is reciprocity.
In a healthy relationship, all parties involved should be willing and able to take care of each other equally. We all have our old wounds and we all need TLC, but if we find ourselves in a situation where we're spending most of our time attending to someone else's pain while they're doing nothing or very little about our own, that's a lopsided and destructive dynamic.
I have to say it. It's almost a cliché at this point to reiterate how it's not a woman's job to fix a broken man (and any additional genderfluid permutations of this), but it does need to be said.
There is a trend I've noticed in some (not all, and maybe not even most) portrayals of the Jill/Chris relationship that Chris is a shattered man barely holding on because of what he's been through over his life, but Jill is the one who can soothe and heal him and remind him of his humanity. It's enough of a theme that when Death Island tried to invert it the result felt weird and out of character for them both.
Jill's been through the ringer just as much as Chris has, if not more so, regardless of whether or not you follow canon or my divergent biography for her. And the portrayals of Jill I gravitate to, and that I've based mine on, show her handling it in a far healthier way: She has her wounds and her scars, but she's still alive. She keeps coming back to do what she's devoted to, and more or less takes life in stride.
But that doesn't mean she doesn't need love and softness. Even the strongest of us still need a safe space to be vulnerable. She has her own needs that must be met, and I have healthy doubts that most portrayals of Chris I come across in canon or fandom would be capable of meeting them. And that just wouldn't be fair to Jill.
That's also partly, I think, why my story has ended up the way it has. Chris certainly could be the person Jill needs: He absolutely has it in him, and I'm always down to ship my Jill with any Chris who recognizes this. But that self-destructiveness has unfortunately become a huge part of the canon character and derived portrayals over the years, even if the endings of neither Resident Evil (1996) nor Resident Evil (2002) necessarily imply that's the road he's destined to go down.
This is something that's built into Ashley's character by default though: It's simply part of who she is as a person that's established as early as Resident Evil 4 (2005), and Resident Evil 4 (2023) more or less makes it her entire character arc. Her relationship with Leon is almost the complete opposite of the unhealthy Valenfield takes: Ashley spends the entire game practically throwing herself at Leon, begging him to let her help him and take care of him. She's afraid she can't do much, because she's a scared and traumatized kid, but she recognizes the severity and desperation of the situation they're in and still wants to do what she can.
She knows what she has to do when the chips are down, and that's what makes her a true Survivor.
Leon though, brushes her off at almost every opportunity, only relenting in the emotional climax where she saves them both from Las Plagas (and again, this is elabourated on in RE4make when there are a number of puzzles Leon and Ashley have to solve together). Leon has his own special cocktail of self-destructive traits, but I'm going off on a tangent: The point is, Ashley would do the same for Jill if she were in that situation with her, and Jill would immediately pick up on and be receptive to that.
It might even be novel and unexpected enough for Jill to momentarily wrongfoot her: She likely wouldn't have been used to that kind of treatment, at least on this team. Ashley's pure care, concern and affection takes a decidedly different tone to Chris' overprotectiveness or the professional camaraderie and loyalty of O'Brian, Billy and Rebecca.