Discounts for late October

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I am planning our vacation for Oct. 17-25. We haven't decided completely on a resort but are looking at the Poly, AofA, or possiblly offsite at WBC or even Wyndsor Hills. I want to get the best deal on our rooms and dining. After doing the math, based on the Disney website pricing, the regular dining plan is definitely a good deal for our family of 5 versus paying cash. If we can get free dining on a room, that would probably trump any discount available as well. I want to book our resort next month so I can make dining reservations at the 180 day mark. Having never stayed onsite, I don't know which resort I should 'bet' on for free dining. If free dining isn't available, what's the chance that a good room-only discount will be available? We have also considered purchasing an annual pass for at least my husband, if not myself, because we want to go back in May 2016. What are your best tips for getting the best deal? While the price isn't the only factor, I don't want to spend more than I have to because those funds can be allocated to more fun things ( like MNSSHP).