Your scenario is one that demonstrates how important Use-Year <i>can</i> be.
We have the same situation.
When we bought in 1997, there was plenty of availability in all use-years, so our guide asked us, "Well, which month would you like?" Not having a full understanding of the "Use-Year Concept," we said, "Uh... I dunno." (try to make that sound as dumb as possible)
She said, "Well, when do you like to travel?" We told her October, so she got us an October use-year. In retrospect, it probably should have been set a few months "beyond" October.
As the years have passed, we've found ourselves booking more and more stays in September. We "did" have to cancel a trip, once. Fortunately, we live close, so we were able to reschedule. We also had the option of sending friends/family over for a few nights - instead of just "losing the points."
Good Luck with your reservation!