I have looked into this and oddly enough it seems to be the embedded EXIF metadata in your image files that confuses the Clip Sport. This data is differently formatted in the file that works (1970.jpg) compared to the ones that doesn’t. The images seems to be created with PaintShop Pro X6 and that software is capable of editing EXIF metadata directly. As a first step though I would like you to remove the data all together on one file and confirm that it works.
The easiest way is to upload the image file 1971.jpg to http://www.verexif.com/en
Select “Remove Exif” and save the new file. Then try to use that image file with the Clip Sport.
If it works, update (or simply delete) the EXIF metadata within your image files with PaintShop Pro : https://www.youtube.com/watch?v=OqN9Cluc1jI