Very interesting question. I suppose if you have determined that the oil is up to the task of a 1 year OCI, it wouldn't matter. The real question is, which "severe" season (summer or winter) is it most important to have the freshest oil. Your seasonal driving habits might matter.
Another way to ask is, which season (quarter) do you want to have the oil in during it's weakest, end of it's run?
1.Dec,Jan,Feb. COLD
2.March,April, May, mild
3.June, July, Aug. HOT
4.Sept., Oct,Nov. mild
For some reason I favor the early Dec. OCI. The oil should still be good during the hot 3rd. qtr. and the "spent" oil will survive better in the "4th." quarter than it would in the post winter "2nd" quarter. Yes...no???
Is there some other logic that says it would be better to have the fresh put in early June?