Question: How did the Waitress at the breakfast place not see Tom, Ken, or Mort at 9am and say nothing of Mort having been in there earlier? Ken and Mort were scheduled to surprise Tom at breakfast, so Tom would have already had been inside at the time when both Ken and Mort would have interrogated him.
Question: Why did the inside of his cabin look like a tornado hit it, was the maid at the beginning just another one of his hallucinations?
Answer: More than half of the movie was through Mort's perspective so to him it wasn't that dirty and I think the maid was real but mabey hadn' t been there for a while then you can see the house through Amy's perspective, near the end of the movie.
Answer: Towards the end, the townspeople had shunned Mort and refused to provide him with any services, believing he killed Amy and the others. The maid was real and probably quit for the same reason and likely feared working for a suspected murderer. Mort, dysfunctional and sinking eve further into madness, was unconcerned about keeping a tidy house.
The townspeople didn't shun him until Amy, Ray and Ken disappeared. His slow descent into madness preceded that. I think she was a figment of his imagination as he slowly goes mad. Or, he fired her because he didn't want anyone bothering him.
Answer: Since Amy was the one to walk in on the mess, that couldn't have been why the housekeeper wouldn't come back. I think she was just in his imagination.
Question: What did the chess set look like in the movie? I seem to remember that it was oversized.
Answer: What chess set?
Question: Why did Mort/Shooter kill Chico the dog? I don't think he wanted to upset Amy, because she never finds out that Chico is dead. She calls his name when she takes the divorce papers to the lake house, where Mort/Shooter kills her.
Answer: "Shooter" (actually Mort), killed the dog as a threat and a warning to Mort, implying this will happen to him if he doesn't cooperate. Mort, as himself, has no recollection of doing this and believed "Shooter" was threatening his life. Mort then reports it to the sheriff, which only fed into his delusion that Shooter was real and shows he's losing his grip on reality. It wasn't about Amy.
Question: What's the back story of Mort and his wife mentioning the previous stalker and how he paid him off? They also mentioned the people who only knew.
Answer: Mort, as Shooter, would have intercepted Ken and Tom and convinced them to go to his secluded property. Also, Mort didn't go to the store at 9. He slept past 10 am.