I agree. And I also think Penn was very much trying
not to create an atmosphere in this movie for those to judge McCandless for his mistakes, many of which were common sense and obvious. (and I don't think you were judging McCandless, just commenting on Penn's choices!)
I'm glad that Penn's interpretation was not to make a hero out of McCandless, he simply painted him as a young idealist with a troubled childhood who needed to break free from his parents and discover who he was and heal. While its sad that he died doing so, I do believe that he found the inner peace on his journey, which was what he was striving for.
I think if I were to have met McCandless on the road, I would have befriended him like the many others whom he met on his road trip. McCandless was a bright little ray of sun in the lives of those he met along the way, sparking a sense of renewal in those who's lives had become stale. I think that was the beauty of his journey.
I think I would have really liked him, and would have probably tried to gently suggest a map, a compass, some better gear, etc etc.
I think it really comes down the fact that McCandless was young and full of alot of trauma/anger/resentment from what he experienced in his family life --I think its hard to understand the state of mind that comes along with that for those who've had good relationships with thier parents. His sister understood that he'd touch down when he was emotionally ready. At his age, being so close to that kind of anger; I can completely understand why he needed to detach and heal and find himself -- he was ready to reconnect with his family toward the end, which I guess makes the timing of his death so tragic for me. I found it interesting that Penn seem's to have gotten alot closer to the McCandless family than Krakauer; and had some very compelling insights.
On line I really enjoyed was "once you forgive, you can love", I think he found that in Alaska.