Greetings, Emily!
I hope you are having a delightfully Disney day planning your fall vacation. September is one of my favorite times to visit the Walt Disney World Resort! Historically our trips have included beautiful weather, lower crowds and gorgeous autumn decorations. September also features
Mickey's Not-So-Scary-Halloween Party -- a must-do event for us!
This question is a tricky, because you run the risk of rooms no longer being available at either of your resort preferences. I would probably wait it out if I was sure I did't want to upgrade to the Moderate Resort without Free Dining. In the past, these special offer dates have been announced around May, and although it is no guarantee as to when or if they will announce it this year, I would definitely keep an eye on the
Disney Parks Blog and the
Special Offers page around then. If an announcement is made, call Disney as soon as possible to let them know you would like to upgrade your resort and take advantage of the deal.
I hope I have been able to help, but should there be anything else,
please let me know. Happy planning and magical wishes,
Lauren