Something I thought about with our 8 night Free Dining reservation was trying to switch it instead to a 7 night and using a room only discount for the last night. You can still choose as many days as you want for your tickets (so you can choose 8 still if that's what you're going for). You'll get one fewer day of meals than you would with the Free Dining, but you might save quite a bit more than paying rack rate. Also, depending on when you're leaving (say, if you're flying out in the morning), this could actually work out better. You can use your dining credits on the day you "check out," so you would still have the ability to use your credits your entire last full day. Then if you're leaving early the next day, you really don't need to use the dining plan anyway. We added 2 nights onto a stay (was a room only, not dining related) 2 trips ago because we had credit card points we could use. I called for our room preferences and had a castmember type it in over the phone, and he also added a note that we had 2 separate reservations so they would see that when they were booking our room. He also told us to say something when we checked in. We were kept in the same room for the whole stay. I think if they can avoid switching you when you have 2 back-to-back reservations, they will try to keep you in the same room because it's less work for them.