Funnily enough I didn't mind Rory's early break downs, because they felt like reasonable reactions for what she was going through and she pulled herself together afterwards. A lot of teenagers would crack at the teasing and workload she dealt with at Chilton and most students have some meltdown or other during their first year of college. Rory's struggles humanized her more than if everything had gone perfectly, and she was sympathetic because she pulled herself up again. But with Mitchum her reaction was totally out of proportion and she didn't learn from it. Maybe if she'd struggled more during s5 (Mitchum, her classes, YDN fitting in with Logan's friends) and built her to her dropping out to reevaluate her life. Instead it was: Things are fine --> Receives one piece of criticism --> Commits a felony/drop out completely --> Lazes around being adored by Logan's friend and the DAR with no introspection for months.
The YDN editorship and Vice-President were the two biggest examples of Rory getting things she didn't deserve or even aim for. Her academic achievements we at least see her working for and wanting very badly, so I don't resent them. (Though Paris should have got Valedictorian). But too many other things just fall into her lap.
Bahaha, I complain about GG so much I have to ask if I ever enjoyed it. But honestly, I wouldn't still be dissecting the characters and trying to fix everything if the show hadn't been good in the first place. It's a sign of how great the early seasons were (mostly 1-4) that I still care about the characters and am invested in their stories even after years of terrible writing. There are a lot of shows that didn't end develop nearly as badly but I gave up on out of disinterest. GG may drive me crazy, but it's still got wonderfully complex characters and my early love keeps me going :D
That's always why I come back to Luke and Jess as well: They brought out the best in Lorelai and Rory. While Lorelai was self-absorbed with whoever she dated and bossed Luke around, he was good at keeping her grounded, called her out on her bullshit and actually enjoyed snarking with her. (Keeping Lorelai on her toes is pretty essential if you want to date her). And on the flipside she was good for him, got him to lighten up and not isolate himself. With the exception of the s6 toxic mess and their flat dynamic in the revival, it's obvious they enjoy the whole "Lorelai babbles and Luke grumps about it" routine and it works for them. Imo the two most telling exchanges about their relationship are Luke building her an ice rink because he doesn't like seeing her sad even though he's Mr Grumpy Grumps, and Lorelai sending Luke off camping only for him to admit he likes her dragging him along to her shenanigans. They're not perfect but imo they're very compatible and enjoy being together, even if they bicker on the surface.
With Jess, there's a pattern of him bringing out the best in Rory, especially when she's at her lowest. (Triggering her returning to Yale, breaking her writers block etc.) I might be in a minority here, but think he had a positive impact on her in s2 and 3, even when their actual relationship was a mess. Unlike literally everyone else in her life, he wasn't blind to her flaws and called her out on them. (E.g. questioning whether she's too sheltered to be a foreign correspondent, pointing out she was in the wrong for kissing him and running). At the same time he was still supportive and truly believed she was capable of achieving her goals and unlike Dean wasn't threatened by having such an intelligent girlfriend (there was a lot of tension from Dean about her Harvard plan, while Jess stepped back and let her make that call herself). Basically Jess managed to rare feat of being realistic about Rory's strengths and weaknesses, but not turning on her whenever she screwed up. Too many people in her life idolized her and then couldn't deal with it when she failed (Lorelai, Richard & Emily, Stars Hollow residents).
I also think it was important that Rory first began bucking expectations because of Jess. Her remaining friends with him over everyone's objections and standing up to Lorelai over the car crash, was pretty significant in learning to become her own person separate from her mom. Yes it was uncomfortable for Rory at the time and she didn't deal with it well, but it was necessary. And unlike her rebellious, "finding myself" period with Logan, her choices regarding Jess weren't destructive or impacting her life negatively. She was still focused on school and hobbies, didn't change herself for him, kept close relationships with her family and friends, and was secure in herself. The worst Jess-related consequence was missing Lorelai's graduation (which wouldn't have happened if she'd picked literally any other day to rebel and see him) and the break up with Dean. (And tbh that split was always going to happen, whether it was because of Jess, her leaving for college or meeting another more compatible guy down the line).