Targets closer than zero?

That depends on how big the acceptable hit zone is.

If its a 8" hit zone....aim dead on. If your threading a keyhole....you need to know your ballistic arc in relation to your sight height.

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Looking directly at the bull through the optic....do you need to hold over of hold under here to hit it?

Just because it's closer in doesn't necessarily mean it's a hold under.

Run your data on a ballistic solver. You will see where near and far zeros are and everything in between.
 
the reason we zero at 100y is BECAUSE everything is a dial up

yes technically its within some distance of 100y either side and that depends on too many variables

and a lot of the time it doesnt matter at safe distances. i.e. a 50y zero in rimfire and a 35y target. the Down measurement when converted to inches is half a bullet width at best