Perhaps.
I tend to side with those who claim that ordering the planning DVD, saving unreserved trips in your personal profile, and maintaining a pattern of activity on their website tends to keep your account in the "tease them with a discount pin" category. My experience is that I'm receiving pins for dates corresponding exactly to the same time periods for which I am researching lodging availability while logged in.
And for those who wonder if having reservations will lessen the opportunity to receive a pin, rest assured this isn't the case. My 2010 trip was on the books for well over a month when I was blessed with a pin allowing me to convert from room only discount to full-up free dining.
But I will agree that the chances of getting a pin are exactly ZERO if you haven't opened a profile and registered an email at the main Disney site, opting in for marketing emails and promotions.