Easy - Saber, because this route like is a fairy tale. Shiro looks like a kid, who believes in his dream.
Normal - Rin, because Ubw is more darker and realistic than Saber's route. Shiro looks like a teenager, who believes in his dream, but understands that it is impossible.
Hard - Sakura, the darkest and cruelest route. Shiro abandons his dream and becomes an adult.
Insane - Ilya, because she is cute and cruel sadist, who, anyway, is very kind. (I cant express my thoughts
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