Hi
I’m not sure why it isn’t working as expected. I have a very similar setup in my books with a text column for content and wide margin for students to make notes; the margin also accommodates author notes or references. The margin box is a text frame with an object style that has Anchored Object Options set to X relative to Page Edge (or you could use Text Frame) and Y relative to the line. The anchor can be positioned at the relevant place in the text, including in a table – in your case I would put it at the end of the subheading paragraph – and the margin box will follow the text as it moves. You can fine tune the Y offset so it aligns with the heading or the start of the table.
Steve’s suggestion works too, and may also make it easier to control the situation when you have categories where the product image is taller than the number of product rows in the table. You have two cases where using an anchored image would require you to apply some manual workarounds: when it causes the image from the short category to overlap the following one, and when a short category falls at the bottom of a page and the image continues below your text frame. Using a table for everything will avoid these.
Nick