I have a WordPress Network install and facebook og:images code setup for the thumbnails.
Any og:images that reside under /blog are not rendered by the facebook debugger. See example at http://developers.facebook.com/tools/debug/og/object?q=http%3A%2F%2Fwww.myjewishlearning.com%2Ftest%2Ftest.shtml – only images located outside this /blog directory get picked up properly by facebook. In this case dark_choc_brownies.jpg is the same image just copied to /test to show that there should be no issue with the image size.
Why is facebook having such a hard time using these image locations?