There is only one scenario where that will not happen and it is when the oil gels under shear at the pump intake. That was exactly the problem that was observed in the 1980s and caused a revision to J300. They discovered that the pour point test did not adequately represent oil that was rapidly cooled. Those goofy "watch the oil flow down the ramp" tests are just as useless in this regard. It's not how "fast" it flows to the pump, it's whether it will flow at all - and this is represented by the winter rating.But if the oil can't flow to the pump fast enough, it will suck wind, not oil as you pointed out. If it's -20F even 0W-16 is not going to flow like it would at room temperature. Nowhere close.
Like a lot of people you're fixated on this type of flow which isn't important. The winter rating represents the actual behavior of the oil near the pickup, so any oil with a 0W rating will have acceptable performance down to the temperature of the test. It will make it to the intake and it will be pumped and it will flow. The test for this behavior is much more complicated and representative than pour point or a YouTube freezer test.