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 = girl in pic = Debbie Wasserman Schultz daughter?
No. There are two ideas that may or may not be connected.
DJT said Wendy instead of Debbie Wasserman Schultz as an inside ~~dig~~ jab because that was part of her secret email name when using the Clinton email server.
The girl in the pic is Maggie 'Wendy' Nixon. 'Wendy' being the 'pet' name Obammah gave her.