I don't know anything about the product you're using, so these are all guesses, but here we go:

My first guess was that the JPEG was too large. But your working JPEG is bigger than the non-working one.

I don't know if the "tiff properties" thing has anything to do with it. Are you sure that all images with that tag are the failing ones?

It's more likely something much more simple. Like the file name. Perhaps this remote doesn't like the commas or the parens or the file name length. Or maybe it's something in the folder structure above it.