A really long time ago, I used to use a piece of software called Real 3D on the Amiga. It was a brilliant little solid modeller, and worked just as one would wish such a thing to work.
Since then, things have changed very much for the worse. Almost no software (certainly none at all that I’m aware of) actually has the ability to do boolean operations well. Sketchup’s “solid tools” tend to leave a terrible ragged mess that needs considerable manual editing to even look right, let alone be accurate. Worse, you can forget about the model ever being considered “solid” (by which I think Sketchup means “manifold”) again, so you can only ever drill one hole in something.
I know there are specific concerns when using boolean operations on polygon models, but why is this always so bad? We used to be able to do this in about 1995. It is a well-bounded problem with a deterministic solution. What’s the issue? Why is this so hard?