MILL-MAX .020 pin in a .026 hole

We have an assembly which we are trying to machine pick and place a Mil-Max pin that is .020 dia placed in a .026 hole. The board is .1125 thick. We have to place 106 of these pins.

Without going into the challenge of getting proper hole-fill to meet IPC class 3, we are not being successful with machine placing into a bare board. I'm aware of the tolerances but was wondering if anyone has been successful with doing this? What needs to happen to be successful?

After putting the board on our CMM and getting some measurements of the hole locations,we have found a range from .002 to .0035 from the gerber data. Still within IPC and board manufactures tolerance. Any assistance would be greatly appreciated.

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