eric -- i agree with a lot of your post.
Chris was disillusioned with society. When he found out some of the details surrounding his father's first marriage, he felt disappointed and betrayed. He seemed to believe he did not need money, relationships or comfortable housing in order to be happy. He seemed to feel that going into the wild would somehow free him from its trappings.
But it's easy to say that a person is disillusioned just because they perceive the world around them differently than you and I.
The author, seemed to see Chris as an adventurer. He dismisses the common viewpoint that Chris did not understand his surroundings or the risks associated with living in the Alaskan wilderness.
others, see Chris as a person with a mental illness who was unable to deal with reality.
I think the outcome determines our perception - we view proenneke as a success. he was better prepared. he has training and mechanical aptitude. we view chris as you said -- naive and foolish to try what he did