I don't have time (at the moment) to read all you have written, its just to long.
However - if your special widget is not drawn by Qt, you wont be able to get to see it through a child widget.
The reason for this is simple - for the transparency to work, Qt must know what is under the child widget, and if Qt didn't draw it, it can't draw what ever should be seen through the child widget.
The problem can be often observed with QGLWidgets as well.
If you have the information in your hand to the drawn content of your special externally drawn widget, you could pass this buffer and the correct region to the child widget - but that will be not trivial and probably not easy.
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