The guy has had some character-building experiences, and that's great.... but he has no business advising anyone on their finances. 

Coming from someone who had admitted to such shame and guilt and even physical sickness from debt burden and money worries, this struck me as particularly ironic:

I have a friend who is going through a tough time financially. He has a high income, but is burdened by debt from a few real estate deals that went south. He continues to take fairly expensive ski trips. That would seem irresponsible in his situation, and maybe they are.

But I now realize that it is not that simple. Maybe those trips are keeping the guy alive, or saving his marriage or keeping him sane enough to work.

I have to question what the author has actually learned.  He thinks... expensive ski tripis are keeping the guy alive?  keeping him sane?  After he admitted that his own debt made him ill?