I am sure somebody would come up with very neat idea, but this is how I interpreted my need for another likely problem. I thought it may apply to yours as well. My problem was to create a frame consisting of members placed with non-perpendicular relation to each other.
So I did a quick and dirty component just to show the idea.
is based upon chopping down your model into prisms then hiding the edges that should not be seen. And the chopped parts will be scaled and positioned according to the overall size of the component. I've used triangular prisms to create wedges and scale/position them. This way you may even create more complex shapes and/or shape groups (a set of holes).
![hole test 01.png](/uploads/imported_attachments/0oKd_holetest01.png)
![hole test 02.png](/uploads/imported_attachments/wArP_holetest02.png)
![hole test 03.png](/uploads/imported_attachments/ku1o_holetest03.png)
PS: I think these efforts are to overcome non-parametric (destructive) model building method which happens to govern SketchUp. I would assume the best practice for more complex hole placements (changing size of the hole according to the size etc.) would be SolidWorks.
hope it helps,
erkan
import directly to your model