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How do I create holes through multiple layers?

I'd like to use boxes to punch holes into the layered artwork below them. I want the result to look exactly like this image, but with the white boxes being transparent holes.

This seems so simple, but I can't find any combination of layers/pathfinder tools/compound shapes/or clipping masks that will produce this result. No matter what, I end up losing part of the artwork (usually the topo lines and the black bar).

What am I missing??

Thanks in advance for any advice.

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