Holy shit. I was expecting something like $200K undergrad to pay for Harvard, followed by $300K for dental school, so that by the time he even got a job he was already like $800K in the hole. But his undergrad was fully paid!!! And heli-skiing??? Dude. This is someone who just flat-out thought he was entitled to a certain lifestyle and was determined to live it, whether he could afford it or not.
I am a huge fan of SLF for people who voluntarily accept low-pay "public good"-type positions, or for people who face some unexpected hardship/injury/etc. that puts them permanently behind the mounting ball o' debt. But spending 25 years heli-skiing and driving your Mercedes -- and then whining about the hardship in public -- is the kind of thing that gives the whole idea a bad name.