Haven't do all the math yet, but maybe it's worth for me pay an extra day before vacation starts just to get FD.
What happens if I arrive 1 day late?
You will be paid in full so they won't cancel you. But you will need to call Disney and tell them you will be arriving on the next day. They will hold your reservation. (I wouldn't tell them that you only paid for the night so you could get free dining though. Doesn't sound good. But you did pay for it.)
do be sure to call on check-in day and tell them you're arriving a day later than expected.
And no, they will not cancel your reservation...this is Disney & you are fully paid before you ever get there. And they are very used to late arrivals and weather delays for transportation...after all they have thousands of people arriving 24/7 from all over the world. Obviously they can't all get there at the expected time.
I don't think you're getting the right information. If you do not check-in when you're supposed to check-in, they WILL cancel you. What you're doing is against Disney's rules. There's a reason the free dining promo ends on a certain date.
I am curious how they hendle a real emergency. I am not booking for free dining, but what if you are, and a real emergency happens. We may drive on our next trip. What if the car breaks down, or the weather delays us?
I hate to do this but we have done this for years. Not to just get free dining,which our travel was during free dining, but to have a room when we arrived. We use to drive and a 12 hour trip for up had us arriving anywhere from 4am-8am. The first time we drove at night we arrived to only be blessed with a room available at AKL. The manager at check in mentioned that one option for us was to pay for the night before. He mentioned for us to just make sure we call and inform them of our very late arrival. We have done this at several resorts and never had a problem. The manager I would speak with would even go as far as tell us the room we were in ahead of time so as not to deal with that. When we drive we just love leaving as we get off work, DH and I trade off on the diving and the kids are asleep most of the trip. We love night driving!!
But yours is a bit different--by arriving in the wee hours of the morning, you are still technically arriving the same day.
When someone arrives, say, much later in the day, it could be considered a no show and cancelled.
IMO, taking this chance would be a big risk. I would either try to arrive the last day of FD, or try for another discount.
I don't understand how my case is different. I may not have been clear. Arriving at 8 am on lets say the 15th when our check in day was lets say the 14th is the next day. I simply would call the resort before we left the house on the lets say the 14th and explain to them we are just getting on the road and we will be 12-14 hours from check in. Now at times we could get on the road from anywhere from 4pm to 9pm so 12 hours from there. We book and pay for the extra night to ensure a room at arrival. Years ago we use to see people sleeping in the lobby waiting on a flight or check in and we would think, I would just pay for the extra day to not have to be here sleeping. I swear we saw 4 families on time at AKL sourrounded by luggage and sleeping on the furniture about 4 am. We mentioned it and the CM said they arrived on late flights but could not get in their rooms till the morning. They were trying to get rooms opened up for them as soon as they could. Of course we had our room waiting on us because we had paid for the day before. I can't imagine.
The new set up does make it more difficult to speak with a resort manager. Please ask to speak with Guest Services and they will get you connected. Also make sure you get the name of the manager you speak with.
Have a great trip and happy planning.