May he be remembered well; he seems to deserve it.
I winced when I got to that. It's sad to think this isn't the first time he's had these thoughts and how long he must have had them. Rest in peace.
I wonder what that meant (appears just after the sentence you quote).
Definitely. He wrote a bunch of blogposts last year on improving life, called "Raw Nerve": http://www.aaronsw.com/weblog/rawnerve