All this was addressed in early CNC evolution with the machines capable of "cutter compensation".
Program it once, .... then adjust the toolpath by a value held into the offset field... at the machine
The trick is to select a programming method and stick to it.
(offset the path in CAM [WEAR, where zero offset value=programed tool diameter ] or offset in the control [CONTROL, where actual tool radius/diameter=offset value])
Safest is using WEAR, where all tools start with a zero offset, and they may need only minor adjustment IF/WHEN necessary.