buying resale vs. direct has nothing to do with UY month...you really can choose either way (although waiting may be involved in either situation).
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 2013 trip and you need to cancel 60 days out (in july), your banking window closed on may 31, 2013 so you'd have to use all of the pts in the reservation before they expire on sept 30, 2013.
if you have an oct UY and an oct 2013 trip and you need to cancel 60 days out, your banking window won't close until may 31, 2014 so you'd have until then to decide whether to use current year (2013) 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, 2014. as stated in #2 above, you can only move pts one time.)
if you have an oct UY and a sept 2013 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, 2013...which is less than 60 days out.
if you have an oct UY and an oct 2013 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, 2014 to decide what to do with them.
more info about UY is here if you need it (you may want to bookmark this thread for later reference):
http://www.disboards.com/showthread.php?t=1942668