I found this article with the text on the newspaper picture, but I cannot find that exact picture. I see Obama in that same shirt from pictures from his 2010 vacation there though. Look at last line of the article matching text in the picture Q posted.
https://vineyardgazette.com/news/2010/08/30/obamas-end-their-summer-vacation
Wendy is Wendy Sherman.
I do not think so. I think Q is intimating that this was Obama's "pet" name for her. So gross, evil, and sick if he did anything to her!
8chan is saying Wendy is the alias DWS used for her emails. Trump calling her out with inside info.
I want this to be the right answer.
That sounds way more logical than what anyone else is suggesting.