This still seems pretty biased. Bench rest at 100 yards? Darryl, IIFID, I think you should shoot offhand at 50 yards against one another, and off a bench rest at 600 yards. Both of you would have a chance to be in your element, and neither one would have to get out of it too far. You should determine how the money goes amongst yourselves, but that is the fairest I can come up with.
