edit mail attachment image

I found it EZ enough to use menu IN MAIL to make sure an attachment is inline, not just a hyperlink

But how to we keep sending this message in reply back and forth with the ability to keep EDITING the PNG image file?

I tried adding annotations from clicking REPLY then dbl-click image> preview opens it> save it by File>close>save

It seems to do so, but who knows what is really happening? Preview is maybe lying, I don't see any annotations show up in the inline image back in Mail.

Mail 4.6

P.S. looks like I am new because by changing AppleID it makes me create new ID here in community....that was confusing!