We have set up several of our websites on Apple News now. For half of our sites (built on one platform), images are displayed in the Article List view 95% of the time. The other half of our sites display an image in the Article List 0% of the time.
However, images are reliably displayed on the Article View page.
The images used are almost certainly NOT the one provided in the RSS feed in the media thumbnail tag; they are almost certainly being scraped from the article itself. Images are set properly in the OG tags.
This behaviour is consistent between iPads and iPhones.
Any ideas would be welcome.
I can think of a couple of things, this may or may not constituent a complete answer, but its some ideas.
Self host the images on a webserver that tracks all requests (nginx - awstats - etc)
Wrap the images or the urls in a tracking url script (can even be monetized) where you submit an image url and receive one in return (called something like In-Image Advertising, or using a link tracker/redirector)
embed a javascript into the theme or what-have-you into this news thing that tracks each image being loaded, ( OR
The rest of these kinds of ideas really very greatly depends on your amount of control, and skills.
Hope I helped you with some good ideas. Willing to help more.