I really hope I'm missing something, otherwise this seems so archaic:
I have a checkerboard I'm drawing in Illustrator (simple example) and I want to wrap text inside the white boxes. In order for me to do any work wrap with Illustrator images I have to have InDesign *guess* where the edges are with "Detect Edges"? If I do that, the wrapping boxes aren't straight at all. I've tried saving to image formats with alpha channels and even those aren't getting picked up. Is it inherently impossible for InDesign to read the alpha from Illustrator? The help file suggests running over to Photoshop to create the clipping path, but I don't need Photoshop for something Illustrator deals with primarily.