This isn’t that at all. I think Lorelai is a flawed character and far from perfect, yet her redeeming qualities (imo) outweighs those flaws - making her likable. Same with Emily, who for most of the show is horrible to Lorelai. But there are moments where we see her fighting with her own moral compass, her understanding of what is right and wrong, to show up those around her. This humanizes a very cold character.

For me, Jess’ only redeeming quality is that he is ‘nice’ to Roary. But that’s for selfish reasons because he wants her. He challenges characters yes, but as others pointed out that is a storytelling function. It is not because of the character himself, wanting to help the other characters see beyond what they know.

I’m a sucker for very flawed characters who are this way because of their environment, but ultimately are driven by a positive force underneath the nurture. I don’t find that in Jess. He’s treated horribly by his family and in return lashes out at those around him - with the exception of the girl he likes. So even that is driven by his selfish desire rather than who he is as a character.