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He's not content at all. Remember how Shirou and Taiga comment that Kiritsugu spent most of his time during his final five years leaving in trips? He was traveling to Europe in attempt after failed attempt to get to his daughter. He failed because he lost all his magical abilities to the curse that later took his life. He never tells Shirou because he could already tell SHirou's idealism and if he did tell him anything he wouldn't doubt it twice to take the goal himself and go barging into the Einzbern's castle only to get himself killed.

You might think this is contrary to what Kiritsugu did later, letting him "take the Hero of Justice" ideal during Kiritsugus death scene, but Kiritsugu honestly believed nothing would threaten Shirou on the same scale as the Grail War. He had taken steps to destroy the Great Grail and put a stop to the War. The War just decided to happen several decades before schedule. Kiritsugu wasn't psychic.

I prefer Kiritisugu as the main more than Shirou.
Basically because Shirou is quite useless and naive (judging from only watching the anime), who knows, I may see what his like in the VN if I have the time.

He's not exactly naive. He just doesn't has a sense of self. He'd sacrifice his own life for anyone. He doesn't put his life on the line to protect Saber thinking he can do better than her. He just doesn't mind dying to protect her...or anyone else for that matter (he pretty much "kills himself" willingly in one route).

They are talking about anime Shirou. He does give out that impression of someone stupid and naive, while in the VN, he's mentally disturbed with a large number of disorders.

Kiritsugu is obviously way better but I personally think he shouldn't care so much about saving people.