Some interesting ideas but quite challenging of my ability. I don't do my own animations and I have no sitting down characters.
I think it could go like this... the user would push the player straight toward the door and find that it will not open. At this point there is no key on the floor outside the cell, but then after a short delay a drunken guard goes past and drops a key. So the player would have to look a second time to find the key. If he attempts a quick escape he is recaptured but if he waits for dark then he gets away.
What the rest of the game is about I don't have a clue.