I was pretty happy with the progression of the Dylan event. For me, I feel that less was more, and the understated acceptance and encouragement Sophia had towards Dylan was a substantive change. Sophia accepting and enjoying Dylan's kneading her butt was a huge step. If we think about it more broadly, we know that Playable Day 13 has a ton of Dylan content, and I think he is now setup nicely to make major gains with Sophia. The event in the park will probably be the moment the door really opened for Dylan, and on Playable Day 13 the door will fly wide-open. I think from here out we should expect significant advancement of the Dylan story.
I agree that, when you compare it to the tutoring story, the Dylan storyline still remains behind schedule, but since I don't play that route it doesn't bother me. If we consider where Dylan was at the end of Playable Day 11 to where he is now, there has been nice movement.