An interesting concept. I gave it quite a few tries but little bro dies of boredom if you don't play the Y-box at least twice, and if you do then you die of something else anyway.
Generally, if a game is designed around experimenting with different options, players shouldn't be punished too hard or at all for making mistakes. I'd say that waiting around for a few minutes is a bit too harsh, so the animations could be sped up a little. Also, I'm not sure what's the difference between actions and actions2? I tried those and didn't really see any difference.
Cute pixel art though! And the creditor's face is quite unsettling, I love them. Could be cool to see them more though.