Just to be fair, Supertramps are not controversial for those very valid reasons; those reasons require thought, empathy and actual understanding of the situation they are in.

Those kinds of lifestyles generally create a knee-jerk reaction to people merely because they are different than the "normalcy". That is clear because, while some people are indeed being lucky/foolish in their endeavours (totally fine by me unless they don't directly hurt others with their choices), some other people have a pretty solid plan/foundation for being able to handle such a lifestyle and people still give them grief.

My lifestyle is far from an extreme one and I still get puzzled questions and the usual "oh, one day, you'll stop and grow up" kind of comments. Imagine if I had decided to drop everything and start cycling around the world.