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Killing his clan? We know why that happened. It was the Uchiha's who were planning a coup and the village elders ordered itachi to carry out the mission. Even then he did not kill his kid brother.
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This is arguing from a consequentialist's perspective. You are sacrificing the lives of an unspecified number of people for the possibility of saving more lives as a result. For Itachi, as a pacifist, and a just war pacifist at that, he would argue that he himself is a villain for taking all those people's lives. Everybody, classically, has a right to life, and he violated their rights for an ambiguous conception of the good. His actions are not justified as they would be if he were truly a hero, they are merely excusable but still immoral.
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While with Akatsuki? We don't have a single evidence of him commiting any heinous crimes.
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This is just a naive sentiment. In order to keep up pretenses we must assume and Kishi himself implies that Itachi had to do acts in line with the goals of an evil organization. Which logically demonstrate a propensity for violence and pain, even though remorse may be associated with the actions.
These cases that you are presenting are just proving my point, he is not exhibiting heroic qualities. He is acting on his own rational self-interest in some instances and in the case of Naruto, how could we know what power he gave Naruto or what his intentions were for the use of said power. Also, most of what we know of Itachi's intentions were relayed to us, the audience, through a biased medium, Uchiha Madara. We cannot and should not take everything that Madara told Sasuke as scripture. Madara has a history of manipulation and trickery that can't be overooked in this context, and Madara's goal at the time was to manipulate Sasuke into working for him.
Once again, I will state that Itachi is an anti-villain. Not a hero. He is a villain due to the actions that he takes, when a hero would classically take the higher road. His methods are villainous but his intentions are contrary to that, aka heroic. Working with a character on a holistic level, any person should be able to derive this conclusion from Itachi's character.