I will usually travel Sept, October, and early November. We may hit an occasional Jan/Feb.
buy a sept UY. there. easy.
Is there a chart for UY/Bank deadline?
remember that all of your pts through 2040 and beyond are already added to your account when you buy the contract. you can call at 11 months out based on your home resort, not UY...
UY month has nothing at all to do with when you call to book.
so you really have a couple of issues limiting you:
1) UY tells you when your pts are valid for stays.
so for a silly example, if your UY month is oct, then your 2020 UY pts are valid for stays from oct 1, 2020 through sept 30, 2021.
2) you can only bank ahead one year or borrow from one year ahead. and once you bank or borrow pts, they cannot be moved again.
so if you borrow your 2020 pts into 2019, they would be valid for stays beginning on oct 1, 2019. but your 11 month window for oct 1, 2019 doesn't open till nov 1, 2018, so your 2020 UY pts are not available for booking until that point.
use year month is mostly an issue if you need to cancel.
some examples:
if you have an oct UY and a sept 2015 trip and you need to cancel 60 days out (in july), your banking window closed on may 31, 2015 so you'd have to use all of the pts in the reservation before they expire on sept 30, 2015. (note that a sept 2015 trip would be in your oct 2014 UY.)
if you have an oct UY and an oct 2015 trip and you need to cancel 60 days out, your banking window won't close until may 31, 2016 so you'd have until then to decide whether to use current year (2015) pts for a reservation in that UY or else bank them to the next year. (you'd still need to use banked and borrowed pts by sept 30, 2016. as stated in #2 above, you can only move pts one time.)
if you have an oct UY and a sept 2015 trip and you need to cancel 5 days out, the pts would turn into "holding" pts so you'd have to use all of the pts in the reservation subject to a 60-day-out limitation - but that won't matter since they expire on sept 30, 2015...which is less than 60 days out.
if you have an oct UY and an oct 2015 trip and you need to cancel 5 days out, the pts would turn into "holding" pts so you'd have to use all of the pts in the reservation subject to a 60-day-out limitation - but at least you'd have 12 months before they expire on sept 30, 2016 to decide what to do with them.
so traveling at the very end of your UY can be risky and result in losing pts in some cases. but if you never cancel, UY will probably never be much of an issue.
the only other reason UY month might become an issue is that some UY months are more common than others:
http://dvcnews.com/index.php/dvc-program-51703/owning-dvc-81414/news-27910/2571-updated-use-year-distribution-charts-april-2014
so sometimes it's easier to find pts to add-on if you own a common UY as compared to a rare UY.