There's always a fine line between being a wandering spirit and a mooch. I used to hang out with the rainbow gathering crowd, and this reminds me of the time my friend, who on coming down from his acid trip, declared that he was going to give all of his possessions away and wander the earth. When I suggested that might not be a good idea, his reply was something like "no, you don't understand, the universe will give me everything I need". I understood why a lot of old hippies end up as forest hermits or sticking to a small group: the burn-outs, mooches, and grifters wear out their welcome very quickly.
That said, I think there's something about going out into a world on a wandering 'quest' that appeals to human nature on a deep level. I'd hesitate to call the author a con man, since you wouldn't call a mendicant or pilgrim a con man. If his motivation was just to squat in people's backyards and mooch free meals until he gets kicked out and then wander around until he finds a new host, I'd agree. But if people want to help him on his personal project of experiencing the kindness of he world, I wouldn't call that taking advantage of people who offer their help freely.
The difference between a spiritual pilgrim and a vagabond freeloader depends on how much of a romantic one is, and if you admire Don Quixote or not.