We have four different Use Years - and we did not use that as a criterion for purchase at all. We looked only at resort, number of points, price and account status (current/banked/borrowed).
In the long run, we ended up with February, March, June and September and the combination has served us well since we usually travel in January, February, May, July, September, October and December. Fortunately, we have never had to cancel a reservation late in our Use Year or past our banking deadline, so that has never been an issue or a consideration.