Is it possible to use the “cut shapes” feature on multiple cutouts at the same time? I just designed a brick wall with 15 windows (for my HO trains) and had to do the “cut shapes” on each individual window. I had grouped the window frames as one unit, but the “cut shapes” feature wouldn’t work.
The shape used as the cutter must be a single closed shape
(emphasis added by myself)
Looks like you must cut each shape one by one.
Have you tried using the “trace Image” tool to see if you can achieve what you want? 
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