Final post tonight before I finish my food and dig into actual writing.
Grace's nature as a teacher is the core part of his character arc. It forms his motivations from initially engaging with the Astrophage to being what he leans on as his 'excuse' to not go on the Hail Mary.
Said students are young teenagers who have grown up in reasonably plentiful times, used to consistent electricity, internet, and food. Those same students will have experienced the very rapid decline of society as food shortages caused by crop failure mount. They are the generation who remember the promise of plenty and saw it wither before them with nothing they could do but hope that there was an answer incoming.
This is also the life experienced by Simon.
Simon was born on Mars and came to live at Eden later. Mars had a population of 7 to 8 billion by our equivalent of 2035 and he was born somewhere in the 2300s~. The game notes that every planet with resources vanished, meaning that was something the human empire was tracking. Mars was the core of human society -- it would have been rife with cities and people everywhere.
Simon's mother tells him 'there's trees on Eden Station', to lure him up there, which can mean two things:
a) there's no trees on Mars, but he'd like to see them
b) Trees are a rare commodity and something Simon likes.
My guess is actually the latter. Deliberately-cultivated gardens on Mars' surface make sense to me. Simon finds comfort in the trees, which, following QR, makes him an ample target for falling into the worship of the Last Tree. The disparity between what was and what now is creates the severity of the loss, and that was Simon's safe place. Now the safe place is gone, one tiny sliver of it remains, and he's clinging on to it for dear life.
Simon is angry but hopeful because he remembers a world that wasn't like this. Some part of him is still saying, 'surely it's still there?' because that's the world he was born into. He wants to keep hoping and keep fighting and keep living because he remembers a world without that constant despair.
What Simon is living is the world Grace's students are living, and the utter hopelessness is what he tried to condemn them to by running. I wholeheartedly believe that he would feel disquieted by Simon's lived experience genuinely not (just) because of the killing, but because it is a reminder of the world he has now left behind. Of what his refusal to go would've left the world with.
Are there students of his who are just like Simon? Manipulated, battered, broken? Clinging to hope? It's a thought he pushes out of his mind but Simon would be a painful reminder, at least for a while.