I didn't read the book but I saw a documentary on...what? Independent Lens? Or POV? Anyway, it thought it was sad and stupid. I grew up in a rough neighborhood and I cannot imagine for the life of me why someone would purposely seek out the things that he did.
I also think it's possible for him to be a feeler but a very emotionally immature one. I know someone who is a feeler (why does that always sound creepy?) and has had no contact with family for many, many years because of how he feels about them.
Did anyone ever read what the park ranger at Denali said about his adventures? It wasn't very flattering or romantic at all.