Lorelai and wealth
I think that my views on Gilmore Girls are always going to be deeply biased by the fact that I think it's fundamentally unethical to be as wealthy as the Gilmores are and that the only ethical thing you can do if you're born into immense wealth is essentially what Lorelai did: run away and reject that life completely.
Granted, Lorelai obviously didn't do that for socialist reasons. I mean the very premise of the show relies on her borrowing money from her parents, so she does still benefit a great deal from the privilege of being born into a wealthy family, and clearly she doesn't see anything ethically wrong with continuing to benefit from that privilege to some extent. Plus, she is probably going to inherit the Gilmore fortune when Emily dies, and though I have no doubt she'll be really uncomfortable with that scenario, I don't necessarily see her giving it all away either.
That being said, Lorelai is also one of the very few fictional characters i can think of who is actually wiling to give up that level of material comfort, by choice, and is genuinely happier for it. There are so many characters on TV like Logan or idk the family from Succession (to be clear, I understand that those characters are antiheroes and the show expects us to judge the shit out of them while also empathizing with them, this isn't a criticism of Succession) who experience immense pressure and abuse from their wealthy parents, but choose to put up with it because they can't conceive of any alternatives. Or more accurately, they can conceive of an alternative, but the alternative they can conceive of would involve risking their access to their family's immense wealth, and they simply aren't willing to do that.
So while Lorelai is obviously by no means an anti-capitalist (I mean she's literally a business major, which in my opinion is one of the worst things that someone can be lol) I can't help but find her choice to actually do something about being unhappy with her life, even when it means giving up the material comforts of the life she grew up in, rather than constantly complain about being a poor little rich girl without ever actually trying to change anything (which is mostly what Logan and Christopher do), to be incredibly admirable and worth celebrating. This is why I will never ever understand why people are so critical of her for making that choice, or for having a generally negative view of rich people. She's literally just correct about that one. Rich people suck. And sure, she may have also been born rich, but she's also living proof that just because you were born into a certain lifestyle doesn't mean that you have to continue living it if you think it's bullshit.
Edit: A lot of people in the comments seem to be arguing against a point I didn't make. As I said several times in this post, I don't think think Lorelai is an anti-capitalist who hates wealth, and I also recognized that she is willing to benefit from her parents' inherited wealth in order to put Rory through a fancy prep school. My point was not that Lorelai hates the concept of wealth, it's that I find characters like Logan, who constantly whine about how hard their lives are, but aren't willing to actually sacrifice any material comforts in order to be happy, infinitely more annoying than someone like Lorelai, who undeniably is willing to make those sacrifices and is better off for it. A lot of fiction, and a lot of fictional characters, treat being born wealthy as some sort of static position that can't be changed, like you just can't control being rich and there's nothing you can personally do to stop actively exploiting people. Lorelai may be an imperfect example, but she is an example of a character who disproves that mindset, by actively making a change that required her to make immense sacrifices. That doesn't change the fact that she is still very privileged in that she has a safety net, and I never argued otherwise. I just prefer her to the alternative (guys like Logan).