He would not have been considerably better at brain-washing Hermione. Others, yes, but not Hermione. Quirrell is Voldemort, the ultimate evil (that we know of). Dumbledore has said that “Evil is that which does not love, and cannot know love without ceasing to be evil,” or similar.
Quirrell has already tried to convince Harry that Hermione is making a show of goodness to further her own ends. If he really believes that to some extent, given that he’s the ultimate evil, he would have a hard time modeling Hermione’s thought process well enough to get it right on the first try.
I wouldn’t say that H&C is necessarily new to the concept of Groundhog Day Attacks. If Quirrell is Voldemort and also H&C, he would not likely have a good mental model of the pure and innocent and good and upright Hermione Granger. It would take him a few tries to find the right levers to push.
But I’m not sure that Hermione isn’t simply under the Imperius Curse at this point. When she’s fighting Draco, she gives her wand a “mysterious flick” in a very un-Hermione-like feint. I don’t know why Eliezer would deliberately place that word “mysterious” there unless he wanted to hint that Hermione isn’t fully in control of her faculties.