When did it begin to feel like Amy Sherman-Palladino begin to lose sight of the characters she was writing?

As the title says when do you think was when ASP was beginning to sight of the characters she was writing? For me it was when she continued to string the Dean, Rory and Jess love triangle by season 3. Rory and Dean should have broken up at this scene

https://preview.redd.it/oe1x52xxno1d1.png?width=2340&format=png&auto=webp&s=7110ae9ded711669e2afd1c18008c6f6f9932c69

This should have been the end of Dean as a character and the love triangle. By then they were just writing contrived drama until Jess and Rory got together.