The thing about Kim Kitsuragi is that yes, he is a deadpan straight man to Harry's eccentricity, but it's very clear that he's not oblivious -- just gifted with an infinite capacity for forgiveness and unconditional support. Which is why it hurts so much to disappoint him.
I think it's crucial, from a design and storytelling perspective, that Kim is specifically capable of being disappointed but also not guaranteed to be. He is legitimately judging your actions and choices, but he also shows up willing to give you the benefit of the doubt—he's heard of the 41st and he's heard of you, so he's inclined to believe that there's method to your madness. He's not a cartoon character who will always react with disparagement or unconditionally support your craziest rambles.
And because he's willing to judge Harry's actions by their intent and outcome rather than their method, he ends up effectively judging the player themself—who is only able to express their intent through Harry's deranged methodology. So when the achievement pops up and you learn that Kim truly trusts you, you as a player feel seen and validated in a way that video games seldom achieve.
What I love about Disco Elysium, (and this is something I came to realize when discussing the game with a friend of mine) is that in a lot of games that throw you into this scenario of "amnesiac discovering themself" is that they're often made to be a blank slate. The actions that you choose change the history and personality of the character, and in a way, you feel like they're a part of you. But when I got to the end, and realized that no matter how I played the game, Harry's story would not change, I realized that you can't really erase or change his past, even if he is eventually a dramatic asshole, or a good hearted detective in the end.
No matter what, Kim, and your team, and even your own emotions don't believe that you are a peon of La Puta Madre, no matter if you beat up Cuno, took every substance you could find, hit on every single person, took bribes, no matter what you did, Kim still believes that you couldn't be that. Another detail I really enjoy is that Kim refers to you as Detective whenever he is complacent or satisfied with your actions, but refers to you by Officer when you are more stern, or less trustworthy. The language is subtle, but it's there.
This game is so beautiful, it's packed full of details and even if you don't engage with it critically there is still something everyone can enjoy inside. I feel like many people drown in their own depressions about the state of the world, but when you strive to do the right thing, Disco Elysium may satirize your choices, but it never decries them. As long as you are a good person, it pushes you to a powerful future. Despite what happens 22 year later, the game directly tells you, that YOU can inspire the change to save Revachol, and the World itself. Listen to the wind.
I NEED YOU. YOU CAN KEEP ME ON THIS EARTH. BE VIGILANT. I LOVE YOU.