Wolf: I believe that you yourself have pointed out the inherent paradoxes involved in phrases like, “Someone who says Ashrei 3 times every day automatically goes to Olam Haba”. So why would this be any different? Nothing in this universe (from our point of view) is absolute. Chazal made absolute statements that were true 99.99% of the time. There can always be exceptions. If this happens to be one of them, then saying Kaddish would certainly help. And even if the person has no Chelek, maybe the extra Z’chuyos would make his Din easier, whatever that means.
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