If a pin doesn't include the days you need then you don't want to book with that pin. I know one of the pp mentioned that the pins are given out at random, but I have received at least 4 different pins in the past 6 months. I received one in the early spring of 2010 which covered June/July/ and August. Around the middle of the summer I received one that covered the rest of the year.
Of course there were a few days that weren't covered. Thanksgiving, Christmas etc. I was traveling in January so I was out of luck on my pin, but my TA was able to get me the 40% off a deluxe anyway which (with a family of 5) allowed me to go from a suite at the all star to the polynesian.
Since I booked that trip six weeks ago I have received another two pins. One covered Jan 2 through mid April and then May 1st through June 6th. I also received another one that covered from the first week of February all the way through September. I can only advise you on what my experiences are, but I registered, saved several vacations, and ordered a DVD and the pins have been steadily coming ever since. Again I hope this helps, and if you don't get a pin try Kingdom Magic
Travel Agency. They were able to get me my deal, and they have been great to work with.