Okay, I can confirm that behaviour. It looks like My Cloud must be processing the JPG file before sending it to the MPW.
I tested using an iPhone 4 rather than an iPad, but My Cloud is basically the same on both, although the interface is a little different.
I transfered three files totalling 5.87MB and they arrive totalling 4.87MB. This is not very good at all. The files are being re-encoded and no doubt losing quality. The resolution stays the same, and all EXIF data is retained. So it looks like My Cloud is basicaly taking the image off the iDevice screen, re-encoding it and sending that to the MPW. Or it could be iOS is doing the re-encoding.
I think this issue would be worth taking up directly with WD Support. You should raise a ticket for it.
The alternatives include using a different App to transfer the files. I just tested File Browser and it transfered the images at the correct size. It looked like it just copied the files, which is what you would expect My Cloud to do as well.
The other alternative, which is what my partner and I do when we are travelling and backing up photos, is to use the Apple Camera Kit, as you do, to preview and view select files on the iPad, but also directly transfer all images from the DSLR SD memory card to the MPW using the built in SD card reader. That way we know for sure that the original, untouched photos are backed up onto the MPW.
It looks like the Olympus EM-5 also uses SD cards, so you could use this workflow. Not ideal, but it works. We shoot in both RAW and JPG at the same time, onto two SD cards, so it makes more sense for us, since My Cloud can’t use RAW files. The RAW images become the masters, and the JPGs the quick review images. You will find some other posts of mine around here talking about how we manage the images, copy speed and so forth.
Perfect level of detail by the way. I was able to follow exactly and replicate the problem easily.