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I wouldn't worry about the tolerance and cross section, they don't effect the toolpath.

Let me clarify what you're asking.

You have an 8 position tool changer

You want to create a tool library of your different drills

You want all the drills in your tool library to be Position 8, but call a different tool offset. 

If my understanding is correct just create the drill, and in the "Post Processor" tab of the tool creation pop-up Where it says "Number:" Enter 8, and for Length offset Enter "X" Where X=whatever offset number you want it to be.