After much time figuring out why I could not get text to wrap around some image but could with others, I discovered it was due to <h> tags. If any fall within any text line next to the image and it’s padding, it forces all the content from the <h> tag down to drop all the way below the image leaving just blank space next to the image.
This causes 2 additional issues:
1. The layout positioning of the text, image, and an <h> in relation to each other is because they are directly relevant an context to each other. Not having them located together makes for bad design flow and content comprehension.
2. To salvage the design I have had to remove the <h> tags that fall near images. In turn this loses the SEO value of that text.