No argument.

The problem is that once you dig through all of this, you're going to find that the problem is that the software is broken. And since it's not open-source, you're not going to be able to do anything about it, except, maybe file a bug report. But you could do that now. And then you're left with photos that still don't display properly. To which the only thing to do is either wait for Apple to fix it or rotate them yourself.

If you're really inclined to pursue it, though, here's what I'd do:

Find two photos, one of which works right, one of which doesn't. Verify that what happens to each photo does so consistently, even through separate uploads of the same file. Then strip the exif headers and create new, ultra-simple ones. Try again. My bet is that something in one of the exif headers is confusing the Apple software.