I don't think he is demented or twisted, more self-absorbed and narcissistic. He thought he devised a fool-proof crime--in person talking with CWW, the burner phones, and being out of town. But, he contracted with a loser and another loser who couldn't plan and get out of their own ways to do a "more professional" job. That is why he is kicking himself. I am sure he thought he had it all bundled up. Hence the "Was it a burglary?" to Dr. P. because it was supposed to be. The forgetting of the life insurance policy to TS's best friend was part of his work. At the end of the day, he thought to highly of his plan to realize that he would get caught ---this was not 1970 but 2015---cameras, cell-phone towers and really good forensics.