I wonder if it's generational. McCandless was six years older than me. That means he was in 10th grade when Challenger happened, 8th grade at the Sarajevo Olympics, 7th Grade in the Lebanon barracks bombing and 22 when we bombed Iraq the first time. We were all right in that formative era when the world changed - in 9th grade debate class I argued against the reunification of Germany. It was the kind of crazy time where Fukuyama was arguing for "the end of history." And I knew lots of guys like this. It was the original GenX "fuck this shit" approach that led to characterization in Slacker, Reality Bites, etc. McCandless is 100% a character out of Douglas Coupland's Generation X (which came out the year before he died). It wasn't that they were accomplished outdoorsmen. It was that they didn't care, couldn't be made to care, and were busy opting out of society 100% because they had no faith that it could be improved or engaged with in anything but a negative way. They weren't "off-the-gridders" so much as they were burnouts. Maybe it had something to do with how much more common acid was back then. That, I believe, is the thing that Krakauer worships. It's the fatalistic attitude that if this life isn't worth living you're better off dying than trying to adapt. Krakauer wants McCandless to be a countercultural hero, not a poacher burnout that doesn't believe in maps. If his struggle is noble his life isn't in vain; if his struggle is ignoble then The Man was right all along and The Man must never be right. Richard Proenneke's book had been out 19 years by the time McCandless headed out. It was a thing. Dick Proenneke basically proved it could be done - and that with aplomb - if you knew what you were doing. But if you know what you're doing, you're not pure of heart or some shit.
McCandless was twelve years older than me. My generation was around for the fall of the Berlin Wall and collapse of the Soviet Union, but I think I was too young to understand the significance of either. My generation saw world events like the impeachment of a president over a blow job. I read Generation X in college, and I agree McCandless would fit in perfectly. I'll have to go back and re-read it. My generation had its share of burnouts but not in a GenX sort of way. Our burnouts smoked pot or because alcoholics and worked dead end jobs, walking away from society only metaphorically. I completely agree with your assessment of Krakauer and the idea that McCandless's ignorance was somehow more noble. It isn't just that a book about a well prepared person spending for months in the woods wouldn't be as compelling, I think Krakauer would be almost disappointed.
I would love to see a Krakauer book about a bunch of guys who have their shit together and triumph over adversity through planning and foresight. But then, that would be a Michael Lewis book. I remember precisely the moment when the world ended. It wasn't the fall of the Berlin Wall in '89. It wasn't the dissolution of the Soviet Union in '91. It was Sotheby's auction of the Soviet space program in '93. Only 45 years elapsed between the first terrifying beeps of Sputnik and the first hit of the gavel dispatching the crown jewels of Soviet technology to the highest bidder but those 45 years defined our lives. My great grandparents escaped the Tsar. We had friends whose grandparents got out of Moldova just in time, taking with them the crown jewels of some lesser duchy. Non-Iron-Curtain Europe was generations back to us and there it was, a blip in the back pages of Newsweek, a human interest story about Gagarin's space suit available to the highest bidder. They shelled the Kremlin and nothing happened. Everything we knew was wrong and there was a lot of searching. it would be facetious for me to argue Christopher McCandless was at all interested in the Cold War but there was a very real sense that the universe was changing if you were young and impressionable in the early '90s.