Gets weirder. If I save either the 8bit or 32 bit versions of the PNG to a file and insert it into the WPRichText as a linked image, it works fine in the PDF (both are transparent). However, for signatures I insert them into the WPRichText as embedded images.
So I guess that would be the difference, and would be why the sample PNG I had was working because it was a linked image and the signature testing was an embedded image.
Something you may want to check out. Why an embedded PNG image needs to be 8bit to be transparent in a PDF but a 32bit PNG is not transparent in the PDF. Both are transparent in the editor and in Print Preview.