A lot of questions about Chris McCandless remain unanswered. Krakauer's account of Chris's final year of life is interesting and as accurate as he can make it based on Chris's letters and interviews with people that knew Chris, but it is by no means a 100% accurate retelling. When writing Into the Wild, Krakauer was forced to make some logical jumps in order to piece together the random appearances of Chris. For me, there are lots of questions that remain unanswered about Chris.
One big question that I have is the same question that Jim Gallien had in the first chapter of the book. Why on earth was Chris going into the Alaskan wilderness with such a small caliber rifle? Along those same lines, why on earth was his gear choice so substandard? Chris had been living on the road for a long time by this point in his life, so on one hand he is quite capable of being a minimalist. But on the other hand he has to understand by now that a few pieces of the right kind of gear can make all the difference in the world.
Another question that still remains unanswered is exactly what caused Chris's health to decline so rapidly in the Alaskan bush? Chris had been living for quite some time on the meager stores he usually traveled with, so how did it all fall apart for him so quickly? Krakauer offers a bunch of suggestions, but none are a definitive answer.