[[ Itachi didn’t tell Sasuke to kill Naruto specifically.
You have to remember, when Itachi said those things to Sasuke, he was acting under a fake persona. This was the path he felt Sasuke needed to take to overcome him.
Normally, yes, Itachi would be against that logic. He wouldn’t, under neutral circumstances, tell his little brother of all people, that he needs to commit murder to become more powerful. But we’re dealing with “villain” Itachi now, who pretends that’s how he got the power, and thus that’s how Sasuke needs to get it. And again, he didn’t know Naruto would become Sasuke’s friend. It could’ve been anyone.
It’s meant to make Itachi look bad. It’s meant to make him look like a monster. A monster who is hungry enough for power that he would sacrifice his best friend for it. Obviously we as readers know that’s not how it happened, but that’s what Itachi wants Sasuke to believe.
At the tail end of the plan, it’s also likely meant to ensure that Sasuke gets Itachi’s eyes. Say that Sasuke did do it, and got the Mangekyo at that time? By this time, he’d have surely gone or was going blind. If we factor in that then, and only then, does Sasuke discover that the cure for the blindness is to take a relative’s eyes, then Sasuke will have to take them, as Itachi intended. ]]