Happy Holiday's Everyone.

I am currently considering a trip and would like to base it around potential free dining options in September or October 2018.
So please help with the possible process:
Do I book a room/package with the September dates I would prefer?
Do I wait and see if any free dining dates will be offered for 9/18 - 11/18?
(If so when are these usually announced?)
Are there any tricks to being offered free dining offers by requesting vacation planning information?
I know and realize that free dining may not be offered in 2018 and it is not a necessity, but I would like to take advantage of free dining if offered as my our dates can be flexible.