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The Buddhist population is too small usually to support local teachers and there is no potential for support from the Government as was often done in the past. If Buddhism is to take hold in the west it will almost certainly need to find a way to support itself.
Genpo Roshi holds these 5 day retreats for 5 people charging $50,000 a piece, the proceeds of which supposedly go to support his other education efforts and he says he doesn't take any of it for himself. Is this a legitimate way to support his teaching or is this sort of thing going too far in commercializing something that should be offered freely?
He talks about it in this interview: http://www.buddhistgeeks.com/2009/12/bg-152-returning-to-the-marketplace/