• do I have to measure the spoke holes for the trailing and leading spokes separately and calculate them separately?

    Yes. As you have found, once you have the right numbers, the difference will very likely be lost in the rounding (for the same reason, we don't calculate inbound and outbound differently on J-bend spokes, even though strictly speaking they are different)

  • if the difference will very likely be lost in the rounding, isn't the answer 'no'?

    No, because "very likely" is not the same as "definitely". At some point, there is going to be an edge case where the correct solution is spokes of different lengths even when the length increment of available spokes is so large compared with the difference in calculated ideal length.

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