Ok, so if I understand correctly, When the text portion would run off page, you want to wrap both the image and the text together.
That means effectively you want to emulate some property like "Keep with Next" on the image.
I haven't tried this to do exactly this before, but I do something similar using a hyperlink. Perhaps you could add a AddHyperlink to your paragraph, add the image and formatted text to this hyperlink, but supply no link destination if that were allowed. If this still wraps improperly, you might be in a position to tweak the Hyperlink rendering to skip the word wrapping step within hyperlinks?
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File comment: Deeply Nested Tables with embedded icon link
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