New purchase memberships might have a harder time getting a desired UY. Depends on your guide and the points they have available. As an existing member they seem to match your UY without much hesitation. It’s good to know banking windows and the cancellation policy to avoid a holding penalty and still have time to bank those points. (Within 8 months of the UY). With all those travel months listed my first choice would be September UY. If you plan to travel more in January than May, I’d go with August UY next. If you plan more May trips than January, I’d go with an April UY next. (There are no January, May, July, or November UY’s).