I don't believe the CMs know any more than we do about future promotions. I just got off the phone from booking our Sept trip and the CM I was speaking to was very nice, but was really pushing the
DDP. I told him I wanted a room and one day tickets only and was holding out and hoping for
free dining again. He told me that for sure free dining was NOT going to be offered for the general public this year. He then said that since I had an AP that I could purchase the DDP without having to buy a one day ticket and really pushed that. When I again told him I thought I'd wait and see if free dining was going to be offered, he again insisted that it would "DEFINITELY NOT" be offered.
Funny thing was, that I called a couple of days ago and got a CM who was "absolutely positive" it was going to be offered in April. Logic says something should be offered for late August-September since it's such a slow time. Disney is smart enough to know that alot of people booked rooms in expectation of free dining and that alot will cancel if it's not offered. We probably would move our trip to a cooler time of the year if free dining is not offered this year..