The correct starting step is to loosen the ropes on the right leg, and then knock around the drill to cut the ropes. To earn the Queen of Ropes Trophy, at the evil doctor's house, get caught by drinking his tainted wine or by going deeper into the hallway, and then break free from the ropes while the evil doctor answers the doorbell ringer.
Afterward, to save herself trouble, she should just exit back out the front door, escaping while she's ahead. During this time, she should enter the bedroom (via the door on the same side where she's been seated) and take the nightclub pass on the bedside cabinet. If Madison refuses to drink the wine, the evil doctor will leave to get the drugs. To earn the Smart Girl Trophy, at the evil doctor's house, refuse to drink his tainted wine.