Another datapoint I just found is that if I use the mobile app on my Android, I can view any picture, even the ones that don’t have a thumbnail. When I view those that don’t have a thumbnail, the thumbnail is created! This seems to be pointing to a Plex Web deficiency and the backend not creating the thumbnails in the first place.
Also, just found @ChuckPa’s post here which contains the issue I’m experiencing. I have “liked” his post.