Vitto32, I think you are right and that this has something to do with the jpg format or the meta data in the jpg.
I created a new post with an image that I knew worked. The preview worked after a Share.
I switched the image to one that didn't work. The thumbnail preview did not show the new image, proving that FB does not refresh the thumbnail data once it scraped the page.
I created a new post with the image that did not work. Image appears on thumbnail selection, does not appear on Share.
I took this image into Photoshop and used "Save for Web" with only the copyright and contact EXIF.
I placed this image on a new post, thumbnail preview works, Share works!
I'm using Lightroom to export all my images. I'll try now to isolate what is different in the image that worked and did not work, at least here is a workaround for new posts. Can someone do this with 2.9.1? I'm still on 2.8 and not upgrading for now.
I probably should do a few more test cases before I get too excited :)