Andrew,
A seemingly simple thing like this has quite a complex explanation.
I don't know much about diesels but reasons between glow and diesel are partly differend. A glow is more sensitive for stability of combustion process because the explosion has to start from one point, glow plug. Diesel instead explodes more spontaniously everywhere in the combustion chamber.
As I see it, due to 4-2-4 -shift (or in general a more rich average run than peak power), the engine is more often out of its comfort zone. And when engine is running rich, you have lots of unburned fuel bouncing about in the cylinder that either burns or doesn't burn, depending on load and temperature situation. I don't think that engine oriention has any important role in how the scavenging works.
But with engine orientation you can affect to what happens in bottom end, there are several places in carter where fuel can get trapped and then get loose when G direction changes. I have found that these things may happen only in outside/inside intersection but not just during static + or - G. It is a quite clear indication of fuel accumulation somewhere.
Also, the gyroscopic precession of engine and prop works the other way too; engine load is differend in inside and outside turn. Maybe it's a very small difference, I don't know. How could it be measured? Or calculated?
But to the original question, cylinder up is maybe the most difficult for starting. L