I think is would be possible to think that IF Tsunade wasn't about to give him a chance. Tsunade was going to give him that date when he came back but he never did so I think that says a lot.
Also I think it is a better theme to have Naruto surpass his master by actually getting the girl and having a happy ending with her, every other parallel with NaruSaku either never gets to the point of romance (JirTsu) or ends with a tragedy due to circumstances (MinaKushi), the best way for Naruto AND Sakura to surpass the old generation is to get to the level of romance and in the end have a happy ending. This allows Naruto to get the girl and for Sakura to let go of her past crush.
Just my thoughts
I get what you meant great post.
I read Strider post he also made some good point but it was more about Sakura not allowing her past to consume and stop her from finding happiness, Naruto to finally achieve what he wanted, save is friend and get the girl, Sasuke would be able to make a better choice with his life and finally accept and acknowledge his friend, sadly this didn't have anything to do with Hinata.
Or... ends up with Sasuke and enjoys an abusive relationship
This was a really silly reply to a great post.
I know you're joking but I still wanted to say that.