If I remember correctly, there is free dining from August 28th to Sept 24th, so as long as your first day of your trip is Sept 24th, you'll still get free dining.
Your guess is as good as anyone's. I'm quite convinced it's coming just as soon as the current offer through 9/24 expires. I don't think they offered fall dates until the summer before. Expect a number of weeks to be blacked out, but it's coming. Disney is addicted to packed resorts and parks.
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