Aside from the above example its hard. You can try joining many hole maker objects as one then perform the boolean.
Or you can do walking vertice face building. There are many many algorithms for mesh face filling. See Blender for example of feature functions.
What youll get are multitude of long tris and these lead to visual problems on the renderer
Also if you dont need to change the geometry but just the look of it, you can simply build a masking shader instead with transparency and double sided render