Actually Mike there IS a way --- I have not done this yet, but someday.......
When starting a pen, mic the tube (I do this) and choose the drill bit that is best (couple thousandths larger) and drill that size hole. Now, if we are going to paint, we ought to be able to decide how many thousandths extra we would like to have. Then, make a chart of "optimum hole size-wood, optimum hole size - non moving materials and optimum hole size painted" with each hole sized for the situation.
As I said, I have not done this yet. I do have SOME of my more popular kits labeled on the bags that contain inventory (large zip locks) with drill sizes written on the outside. But I have not made large numbers of pens this year, so those drill sizes COULD change when we are getting into production for Christmas.
This WOULD be a pretty fail safe method, I think.