Many recommend a use year that begins shortly before you usually go. The only reason for that is to be able to bank points if you have to cancel. By example:
Assume Dec use year and you want to go in Nov 2012. You call 11 months out in Dec 2011 and reserve for Nov 2012. You use your Dec 2011 points for that trip which would be your current use year points for that trip since your 2011 use year ends Nov 30, 2012 and your trip is in Nov before then.
Come September, you learn you have to cancel. Points go back into your acocunt as they were, meaning as Dec 2011 use year points that expire Nov 30, 2012. Under the banking rules, you can bank any or all of your points by the end of your eighth month of the use year. For Dec 2011, that expires July 31, 2012. Thus, you cannot bank your points when you cancel in Sep 2012 because you are beyond the banking deadline. As a result, you have to use those points for a trip that ends by Nov 30, 2012 or lose them which is likely going to be hard to do if you are in Sep 2012 and had to cancel a Nov trip. Thus, you have only two months to use those points andlikely won't be able to do so.
Now assume you have an Oct use year and want to go Nov 2012. You call 11 months out in December 2011 to reserve your home resort for Nov 2012. You use your points that will be coming Oct 2012 which will actually be your "current" use year points for that Nov 2012 trip because it occurs during the use year that runs Oct 2012 to Sep 2013.
Come Sep 2012, you learn you have to cancel. Points go back into account as they were when you made the reservation-- as Oct 2012 use year points. You now have little risk of losing them because they can be used from anytime from Oct 2012 to Sep 2013, or can even be banked into your Oct 2013-2014 use year by July 2013. Thus, you have over two more years to use them if you cancel in Sep 2012.
That is the reason people recommend that you get a use year that begins shortly before time you usually go. Nevertheless, that may mean little as time progresses since your usual time going may change.