So I am at a loss as to how to correct the issue ... if the Jetpack Publicize links work in the Debugger, but not in actual use ... I don't know what more I can do ...
There is not much more you and I can do, I'm afraid. Only Facebook has the power to use the Open Graph data associated to your posts, or to ignore it. There is no other way to let Facebook know what images are to be used on post previews.