Hi, Michelle! I hope I can give you an answer that will clear things up rather than muddy the waters even further!
If you are planning to use the annual pass holder discounted room rate, you would not be eligible for any FREE dining promotions. The free dining promotion being offered requires the purchase of passes and a minimum number of nights accommodation at rack rate.
If, however, you are just booking the annual pass holder discounted room, and want to add a dining plan that you pay for, you can do that. I just called dining reservations to verify this and spoke with two separate cast members, both of whom assured me that it was possible to book your AP discount, and still purchase the dining plan.
I hope this helps with some of the confusion!