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It was not difficult for Itachi to kill his parents, although he didn't kill them because he wanted to.
He saved them for last not because it would be most difficult to kill them, but because it made the most sense. He had started from the outside, the cousins who barely had the Uchiha traits, and worked his way inward, from in-laws to aunts to grandparents to parents. Slowly as he went on, his blades slicing through the familial bonds, the faces became more and more familiar, until he was greeted by one that was nearly his own – a woman, pale and beautiful, who he loved and hated at once, violently and with perfect purity, and so wholly that his only release was in her death.
He didn't kill them because he wanted to, but that is not to say he didn't enjoy it.
It wasn't about what he wanted – wasn't about the way the blood streaked across his mother's mother-of-pearl skin or the way his father's face contorted in agony, fear, shock, disgust (he loved and loathed at the same time, making it one emotion). It wasn't about the thrill of killing in mockery of the lesser Uchihas, nor was it about killing for the sake of honing his skill or the emotionless edge of his blade. It wasn't about detachment. It wasn't oedipal revenge.
It was merely business.
His purposes and the purposes of his organization called for their strength to have no competition. No equal. No living blood. The remaining members of his clan, the ones that bore no blood relation to him and had no special powers, were killed to keep the secrets of the Uchiha secret – all of them. It was better to make a clean sweep. It was insurance for their plan. He would walk out of the Uchiha compound that day confident in the fact that he was the only bearer of the most secret knowledge. He was the greatest of all of them and the most special. (Always had been. Always would be.)
His parents were a liability to him for another reason, though: they were the only people in the world that could draw emotion out of him. His father was the only person who had ever made him feel shame, or some feeling as close to shame as Itachi could come. His mother was the only person capable of making him realize that people other than himself were people and not just characters in the sick play in his head. For that, they had to die, violently, and to fulfill the needs of his imagined play they had to die dramatically in front of each other, and he had to see the horror in their eyes as they comprehended who was holding the sword. And because he had other purposes to fulfill, it had to be in front of Sasuke.
If there was any one thing he wished he could change about that day, it would be his little brother living on. If it were absolutely up to Itachi and his emotions were allowed to dictate his actions, Sasuke would be nothing but a bloody smear on the tatami mat, a splash of red on the wall. His whining permanently silenced.
Unfortunately…
He loathed it, but as long as he had searched for a way around it, as long as he had denied the inevitability of his blood's one weakness, there was nothing to contradict the simple fact that the more he used his Sharingan, the weaker his eyes became. By now they had lost almost twenty percent of their power. If he kept up this lifestyle, he would be blind before he was forty. The advantage of the Sharingan was undeniable, but the cost was steep.
It was all right, though. He had another pair.
And he had seen to it that their caretaker would bring them to their full potential.
And then – how convenient – Itachi's new eyes would come to him on their own.
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