Remember that when your use year is has nothing to do with when you book. Only your check out date determines when you can book. The use year only determins when you can bank and when new points come into your account.
I agree with the others, that if you are planning to usually use your points for November trips, and October use year would be good, because in the even you would have to cancel a trip, you would have plenty of time to re use those points or bank them. If your use year is December, those points would not be available to bank should you need to cancel, because you would be past your banking windows.