I'm sorry to hear that people are still having problems with this so I just had to reply.
I too have a split stay in August -- not because we are trying to beat the system with free dining, but because I am a DVC member and we want to try out 2 different resorts -- Kidani Village and the treehouse Villas. As a DVC member I can't even get free dining.
The date I could make my ADRs was before the first day of the free dining booking so based on my experience and that of others who reported here, this policy does not seem to be related to just free dining, but rather the way the new dining system works and how you have to give your reservation number. This was in fact the explanation I was given.
I and many others had problems booking dining for split stays before the first day of free dining ADRs. Some reported success and some did not. It seemed to depend on the CM you got. The first CM I spoke with would not make anything past the last day of the first ressie. It definitely can be done and the CMs who did it for me (one regular dining CM and one in guest services) did not say they were doing anything that they weren't "supposed" to do. They just said it definitely was a problem with how the new system is designed.
Many people do split stays for many different reasons and I don't think it's fair that we lose our 10 day advantage because we want to stay at 2 different resorts. Day 1 should be the day you arrive and it should not matter how many places you choose to stay. And I think it is even more upsetting to people who are reading that some had no problems or had a CM that did it for them while others could not. Everyone should have the same policy.
Okay, I feel better now that I got that off my chest
I just feel so bad for everyone who reports that the CM won't do this for them. Not everyone is trying to override the system. We just want to make ADRs so we can have a magical trip to the world, that's not too much to ask, right?
As the person responsible for making the ADRs for our party of 8, I just wanted to make sure we got everything so we could accommodate everyone's requests so that everyone will be happy
I just hope they figure this out soon and have one policy for everyone to follow. Good luck to those who have split stay ADRs coming up soon. Hope you get what you want