One of the problems one could say of Heavens Feel is that it isn't really interaction, struggling with, or exploring an answer with Sakura that brings a change in Shirou.
Its horny, and the sort of need to protect Sakura from her lack of agency and the evils shes pushed in. It has a lot of great moments, it uses some characters fantastically (Kotomine). But it fails Shirou, and most of all it fails Sakura in a few core ways like this.
You could say that Nasu figured he'd try to flip it on its head by making the heroine an antagonistic force (already been done in Tsukihime mind.) But you can have a antagonistic heroine of a route interact with, push and force development/answers from the protagonist!... After all the heroine of UBW, Archer does just that very well prior to Heavens Feel