This is going to sound mean, but I can't help you if I don't know what I am looking at. If you are going to hold the pen in your ass cheeks when you draw, please use your hands to type comments as to what is what. Since the goal sounds vaugly complex I vote you Keep It Simple.
Maybe I'm not understanding the question/drawing, but I think your trying too hard. It looks to me by "overlap" that you just want that image in the circle to come down into the same area as the text, like the bottom half of the circle is sitting on a different background color. That would all be done with image editing,…