He also enjoys feather and unarmed clicks, that's why he set up the booth I assume.
On the lack of control the game gives you, he can't actually double your money.
The game itself and the mechanics guide you toward causing more pain and misery which the narrative punishes you for. You are being punished for playing in the way which the game pushes you to do.
Unlike Deltarune where the sparing and recruitment mechanic guide you to making the world better and subsequently being rewarded by the narrative and getting to have a more fun experience.