Hi TFK,
If I make any changes on your little quiz, it would be to say that every pair of objects (arrows, bullets, cannonballs) falls to the ground at the same rate. I know that if you dropped a piloted glider plane off a cliff and also towed another piloted glider plane up to 70 mph with an airplane out over the cliff and released it at the same altitude as cliff's edge, the pilot of the plane-towed glider could convert some of the horizontal momentum into lift, which would give that pilot an advantage over the guy who just went over the cliff in HIS glider.
But with a bullet, or an arrow, I'm thinking maybe there is some lift that comes from the feather or the spinning bullet, but I can't see it in any obvious way. That's why I might just consider defaulting back to every pair of objects falling at an identical rate to each other.
And this is why I'm an empiricist... these thought experiments are good learning tools, and they generate interesting hypotheses, but really now, until you shoot/drop two ARROWS etc. you can't really know, can you? Logic and thought can be better used to interpret and analyze data from actual experiments. Make your conclusion first and then try to fit the facts, and you get reverse scientific method. That's why Aristotle said a spider has six legs, and why... oh, never mind.