Melinda-
You are planning to go to Walt Disney World Resort for the first time! Whaoo! I am so excited for you. October is going to the be an adventure for the ages. Your daughter will be enchanted by Cinderella Castle, swept away by the Magic Carpets of Alladin and jumping for joy when she meets Princess Anna and Queen Elsa.
A rule of thumb for tickets is if you are going to Walt Disney World Resort for 10 days or more then an annual pass gives you the best value. Annual Passholders carry many benefits.
If you think you will return to Walt Disney World Resort any time before October 2016 then an annual pass is the best value.
This is a tough questions because the "free dining" is applied to certain resorts.Free Disney Dining occurs periodically but historically offered in the fall sometime during September to December. Promotions change every year so keep your eyes open in springtime for the details. My fellow panelist
Kimberly has some great insight on "Free Dining".
Disney does not combine discounts so you will unable to get free dining and an Annual Passholder resort discount. I my opinion I would contact a Disney travel specialist and discuss the dates you wish to visit and any passholder discounts for comparison, book a resort and dining plan for those dates and only pay the deposit. This gives you the best option whether or not to keep the dining plan based on future promotions. Your Disney travel specialist will guide you through this process at no charge. Now that’s a deal!
Enjoy making many Magical Memories!
Jason °O°