While it's true that he should have had a better plan to protect his lover, I don't think he went after everybody for revenge, but to "make sure it never happens again". He was just covering his tracks, and those guys had to go, because they knew his name and address.
Also, he didn't leave the Big Boss Client alive out of mercy or sloppiness, but because his death would have caused too much commotion - and he had left too many traces on his way to the Big Boss. His plan had always been to scare him sh!tless, not to kill him.
I believe everything he did after the botched job and subsequent attack on his home was just his calculated strategy to minimize the future risk for him and his lover.
Dude is not boiling under the cool surface. He's just a clerk through and through, a tiny insignificant agent of death, a barely registering cog in the grand scheme of things.
It's the least glorifying hired assassin movie I have ever seen.
And I'm not sure I loved it either, it was too - like you say - hard to root for the guy, due to little context and his very monotone personality. But it WAS special, and it's still something I might think of whenever I bump into an assassin movie again.
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