???
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get a picture of a go go dancer and import into sketchup.
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Size it so the picture is the size of the window that you want.
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Position the picture where you might want the window to go relative to your surface but a distance in front.
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Explode the image.
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Carefully draw edges around the shape of the go go dancer in your image file until you have a closed shaped outline and surface of said dancer. Also ensure that you have a rectagle shape drawn on the surface outside of the shape.
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Push pusll the shape that you created through your surface.
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Select the surface and the push pulled form and "intersect with model"
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Erase the form and it's edges leaving the 'intersected" outline on your surface. Erase the surface of the window or push pull it in for an indent. This can work with a wall thickness too if you erase the forms push pulled on either side of the window but leave the bit inside the wall thickness.
Is this what you were getting at?
