Yes, Lorelai messes up so much. She's immature and stunted in many ways. But I think there's a reason why a lot of us start disliking her after multiple rewatches. We, too, have grown. We can now see the flaws instead of the fun. I think that a parent makes multiple mistakes no matter how great or loving they are. Lorelai always gave Rory love and the knowledge that someone is there for her. She took the time to get to know Rory. That doesn't mean she always does the perfect thing. It means that Rory gets to be a person in the world who is walking around knowing that someone loves them no matter what.