No he doesn't. He did it with Claire, but that's his sister, so it's completely understandable. He didn't cradle Richard because Rebbecca already had his head in her lap while she tended his bite. With Rodrigo he just propped his head up with his hand, affectionate but under no circumstance was it as intimate as Chris with Jill.
That Claire is his sister doesn't mean anything. I know siblings who wouldn't even talk to each other if their lives depended on it, so there has to be an emotional relationship between the Redfields to begin with. Chris especially cares for the people close to him, and I never denied that Jill is closer to him than Rodrigo or Richard are, so of course he cares for her more than for the other two. But the tendency to care for people
in general is there, within him, and there's nothing romantic about that. Since videogame cutscenes have become as cinematic and realistic as they are today, people tend to read a lot into everything, especially when they are fans of a particular idea, for example the idea of Chris and Jill in love. I am a fan of the idea that Chris and Jill are like Harry and Hermione, they have experienced a lot together and would risk their lives for each other, and how many fans wanted them to be together, but in the end, they married other people and remained soul mates forever.
And everything you say about Jill's personality in three paragraphs is just what I said in three sentences: She's the
good girl. She protects people, she's smart, she knows who to trust, she's aggressive towards people she doesn't trust, she risks her life and even dies for others... in short: She does everything you would naturally expect from a true hero, no more, no less. And that's where the story ends. She has no flaws, no dirty secrets, she never fails, she's just perfect. Of course some of these traits apply to the other characters too, after all they're not the heroes for nothing, but everyone else has at least
something that tells them apart from the typical super hero, and sorry, I just don't see that in Jill. All I see in her is much potential that the developers don't use. Jill is not the only victim of this, but the gravest in my opinion.
You don't have to agree with me, but just like you, I've been playing RE for a very long time, and as an author of novels, I enjoy observing characters and their behaviours, so please don't think I only said that to anger Jill fans.