Plot hole: On the bus, Ray has a prescription medication. Where did he get it since he broke out of the hospital?
Plot hole: At the end, Julie doesn't notice the muddy footprints on the floor or wonder how the window got open? And Ray doesn't say a word when the bathroom door shuts by itself?
Plot hole: After the Hook Man kills Dave, he uses the pickup driving toward Ray that knocks him off the road, and knocks him out. The Hook Man could just walk to an unconscious Ray and kill Ray easily with his hook.
Answer: I think that Estes already knew that Will was Ben's son. He had made a comment about a man (Ben) killing his wife (Sarah) in the same room Julie and Will was staying in. He also makes a comment about Will having his mother's eyes. So he probably recognized him. He also knew that the answer they gave to the radio host was wrong, and that proved it was a set up from the beginning.