I do like reading case studies like this, and I find myself of two minds:
On the one hand, the guy acknowledges that -- looking back -- he made thousands of small decisions that seemed right at the time, but hurt him in the long run. In that, he seems to acknowledge that he himself is the source of his troubles. It sounds like he knows on an academic level what went wrong, but he sounds a bit like he's telling someone else's story.
On the other hand, I can't help wondering, "What could he have been thinking?" He was earning a good salary, yet he was living in a very expensive house, in a very expensive town, supporting a large number of children and a non-working wife, choosing to quit working without a real plan, and more. Did he never consider selling the house while it was still possible? Did moving to a less expensive area never occur to him? At some point, didn't he have the good sense to question these choices? He didn't have to do everything right -- if he'd just done 1-2 items differently, the story could've been so different. For example, if he'd moved to a less expensive area when they quit working, things would've been different. If his wife had been working, they likely wouldn't have lost two salaries at once. Just a few more realistic choices would've likely kept the family together and him from sleeping in his van.
I don't know whether to feel sorry for him or not, but he is a good cautionary tale.