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2 people have won in the history of "Sasuke" (finishing late doesn't count..). When someone wins they break the stages down and redo them to make them harder.
"Kunoichi", the Woman's version, was cleared 3 times by the same lady in a short period of time. Since she stopped appearing, they drastically LOWERED the difficulty and 2 women cruised through the final in the last event.. I'm guessing they are going to raise the difficulty again after that.
The difficulty factor is part of the appeal.. Even getting to the Final Stage is rare, but clearing it makes you a borderline living legend.
There isn't any money involved (I think there should be), but the guys that are consistently top competitors seems to do better in their careers or get local Commercial gigs and things like that. Its kind of a hobby/challenge/obssession for some of these athletes (many who never played a professional sport).