James, I haven’t tried your Steps to Repeat, but if I create a new Blank Website, draw an HTML box, command-E to import, navigate to an image, bang, the checkboxes vanish.
This is on a iMac (Retina 5K, 27-inch, 2017) running 10.13.2, Default Folder, Freeway Pro 7.1.4 (previous versions 6 and 5 show this as well).
It happens when the Open/Import dialog is resized to show the preview of the image.
Merry Christmas everybody!
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