308Loader,
What does a new, never-fired case look like on the comparator? I believe you will find it at least 0.005" shorter and that you are not resizing fully. Keep in mind that as a case enters the sizing die, the sides make contact with the die first, so you are actually squeezing the case narrower and longer at first. Contact with the die shoulder then pushes the shoulder back. You may simply have not pushed it back as much as you intended.
If that is the situation, and if you have already tightened the die down as far as it can go in your press, then I would suggest removing the decapping pin and expander and using a shim under the case to set the shoulder back another thousandth or two for your chamber. You would then have to expand it separately afterward. I use the Redding body dies, which don't touch the neck, to avoid this issue and let me use a shim, but it's still an extra step. If you know your sizing die is already turned past solid contact with the shell holder deck and you see no crack of light between the two when you have the case run all the way up into the sizing die, if you know someone with a lathe and toolpost grinder, they could shorten your sizing die by a thousandth of an inch or two, which will set the shoulder back that much more. They could also just grind that much off the shell holder deck. Indeed, you can do that with wet/dry paper spray-glued to a sheet of plate glass.
Unfortunately, the 2.050" number is not a usable absolute measure, as the comparators generally have a little radius at the mouths of their holes that cause them to read anywhere from a couple of thousandths to a dozen thousandths shorter than actual value. Without a headspace GO gauge to use as a reference to compare your reading to, we can't really tell how close the 2.050" number is. I can say that I would expect new brass to be about 2.047" in an absolute measurement and that, allowing for the comparator hole radius, yours is probably at least 0.005" bigger than that.