Working under time pressure for any game is more than familiar to me. Still, why did he sleep from Day 7 all the way to Day 5? 😅 And I think the idea of drawing in the game is brilliant. The horror moment for me was when a screen identical to the Ren'Py error screen popped up. I couldn't believe I was almost at the end and the program had crashed :)).
But is the ending basically about entering an endless loop that starts again after Day 0?