Hi Kevin, I just finished getting some help to send my newsletter like what you describe. I am only interested in a once a quarter newsletter, but the concept is pretty much the same. I used a VA (Virtual Assistant) to do the conversion of my newsletter that I created in Word, emailed it to her and she emailed it back so that I just forward it to my email list.
I know there is software out there that will do what you want but it is very expensive from what I have found. With what I have, I can add above and below the image that cannot be changed.
Here is her email address, won't cost anything to ask.
MyVA@MarshallVirtualAssistance.com