Using the default presto setup that came with the device, I cleared out the local gallery folder to put my own images in.
I then just decided to put them on an SD card. I encountered errors where the images wouldn't display (initially due to .jpeg file extension) and then other issues opening the files.
This seemed to be due to the SPI bus getting into a bad state and j.open_file not liking the SD card. The fix was to read the image into memory first and use j.open_RAM instead.
I have a PR with this change in place. Hopefully this can help anyone else with similar issues.