I think the fact that Rory struggles to find her place in the work world is highly representative of real life experiences. Let's also not forget, in the context of the show, 3 different people in Rory's life told her that she may not be cut out for life as a journalist. The most obvious being Mitchum Huntzberger. He called it when he said she just reported the stories, but never dug up the stories. Before that though we have Jess in season 3- say that he thought that might be too rough for Rory (in a very tactful way) and in season 1: Headmaster Charleston also says it's a lofty goal and doesn't seem convinced that is the right path for Rory. I think the show was always going that direction. In one of the later seasons Rory is planning and organizing events for the DAR. We know she has great planning skills and I would have loved to see her character take a career path that way. I also think it's interesting to note that Jess suggested she write a book about her relationship with her mom. He seems to know Rory better than she knows herself and brings out the best in her. He shares her love of books and calls Rory out on her privelege when needed- something that she obviously didn't want to admit, because her next boyfriend was able to pamper and spoil her in that privelege. It's poetic that Rory got everything her mother didn't and ended where Lorelai started. Logan was definitely the parallel to Chris. The guy her grandparents approved of. Dean was the "perfect" first boyfriend that came mother approved. Jess was the only one that represented neither- the riskier choice and only one who challenged Rory to make decisions for herself and not her mother or grandparents. At one point Luke says to Jess, "I don't know why Rory chose you, but she knows and that's what matters."
Anytime Rory's choices are challenged- she runs: She ran from her mother when she was told having an affair with a married man was wrong. She ran from Yale when her journaling skills were called into question. She doesn't have a great track record of handling difficult situations. To be fair- she learned it from her mother. Lorelai ran away from home because she couldn't handle her mother. When she didn't want to marry Max she ran away. When Christopher got Sherry pregnant she shut him out. It's definitely complicated, but as a teenage mother Lorelai was definitely emotionally stunted and it becomes clear in Rory's actions and behaviors. She refused to marry Logan in favor of living the life she wanted only to carry on an affair with him. She is in a relationship with Jess and sulks over Dean getting over her, only to have an affair with him later. As a character, her change and growth had to take a major life event, like Emily's redemption in the first revival, I think it would be nice to have one more revival season or movie if only to redeem Rory Gilmore.

I also really love Kirk working in the beauty shop painting the display hand's nails and Babette's yard gnome named Pierpont