I spent three hours debugging this problem as well.
I had a 2-page Word file that was giving me the "cannot send" message when using HTML.
The post saying that changing the font helped someone clued me in that perhaps the Microsoft software is having problems with certain ASCII characters, likely invisible ones.
Changing the font was not an option for me because I need to use our company fonts for correspondence.
I delete the second page of the 2-page letter and was able to send the first page, so I knew the problem was in the second page.
That page had been created by copy/pasting the contents of a PDF file into Word (since Mail Merge on Mac does not support attachments). I concluded there must be some unseen content that was causing the error.
So I copied the text into e-mail and then copied that back into Word using "Paste and Match Style" to remove formatting.
That was able to send without any errors.
Then, I slowly (painfully) had to rebuild the styling of the document, checking periodically to see if the new font or bullet characters were causing an error. I was able to rebuild and send the 2-page document after this long, arduous process.
Hope this helps others.