1: The error appears to only happen with JPG; I was not able to replicate it with PNG.
2: Intermittent is by far a more accurate description.
3: Originally, these files were imported from my iPhone. They were then moved to my hard drive, where only then I began editing them. So I can't exactly pinpoint the original moment when the problem started.
Sidenote: I did reinstall my OS recently because I needed to revert from a glitchy Safari beta. So one would think that my mac should be error free after a fresh reinstall.
4: Yes, it is peculiar. This problem happened immediately after hitting save. To add on, upon quitting Preview with multiple images open, I get small text windows popping up and down from Previews toolbar, saying "Checking for unsaved data".