So the problem appears to have been a simple timeout. If I try to upload 4 images at once, it fails. If I do one or two at a time, it is fine. Also, if I start with small images it is fine.
This exposed another issue. While I have set the option to shrink the images they are not being shrunk at all. FTP info in PM.
In addition, the way your Update pages are created, there is no option to delete an image. I can only update an image or leave it as is. That is not my primary issue as I can create a page to do just that but it should not be necessary. Deleting an attribute of a record is a legitimate part of updating.