So it will work even if our checkin date is a blackout date?? i haven't heard wether you can still apply the discount to the whole trip if you check in on a blackout day.
I had this same problem last year for free dining in December. We checked in on a 'blackout date' so I ended up having to make two separate reservations. For the first three days of our trip, I ended up paying out of pocket for meals and then had to book a second reservation for the last three days of our trip which included free dining (because you have to have the dining for every night of your reservation). And in order to do the free dining, you have to purchase at least a one day base pass too. Slightly inconvenient to do it this way, but it all worked out for us. We were staying in the FW Cabins and we got to stay in the same one. All we had to do was re-check in in the middle of the week. Just call Disney when you are going to book FD and explain your situation. They'll work with you on trying to keep the same room. Hope it works for you!