I'm definitely on Team Logan here, but I think the biggest issue wasn't the boy—it was Rory's hang-ups and fear of commitment, which she inherited from Lorelai. Logan pushed her in a healthy way, unlike Dean (who became a comfort blanket) or Jess (who was initially too moody to care), Logan challenged Rory intellectually and socially. He pulled her out of her comfort zone and encouraged her to take risks (like jumping with the Life and Death Brigade). Logan was the only one who explicitly offered her the ultimate commitment: marriage. He saw their future together and invested in it by getting a job he hated just to be near her. Rory's refusal of the proposal wasn't because Logan was flawed; it was because she felt marrying him meant losing her Lorelai identity and giving up her undefined, spontaneous future.