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Disney Discounts prediction

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I just started to plan and I am a little overwhelmed by the options. I see that there is a free dining option available if you book by the end of October. Do you think that if I wait longer than that, they will offer the same or perhaps a better discount option? A friend said that a few years back they had a deal where you buy a certain number of days and get a few free. We are open as to dates since the kids are small.