Hi, Amanda!
I completely understand your desire to be a bit more flexible because you'll have a little one with you on your trip to Walt Disney World; great point!
However, September features the
Epcot International Food & Wine Festival, which is so popular, some Guests schedule a visit just for this event. This often results in many of the most popular dining locations booking up well in advance. In addition, if you do travel to WDW during
Free Dining, imagine how many
other Guests will be taking advantage of Free Dining as well; many of them will make Advanced Dining Reservations well in advance of their stays, too...up to 180 days prior to check-in.
Here's what I recommend: at the 180 days to check-in date, book some ADRs, one per day. Decide which park you'd like to visit each day (I look at park hours, crowd-predictions, variety of park per day) and place a convenient ADR in or close to that park. When my guys were little, we'd book a very early lunch or a very early dinner, so that naps could still take place and tummies weren't yet starving for a meal. On a day with a lunch ADR, we'd visit a Quick Service location for dinner; when dinner was an ADR, Quick Service lunch or breakfast is the way to go. This plan will also cut down on the amount of time you spend waiting IF there is an available walk-up ADR. Plus, if you wait until that day to seek a Table Service location, the only times available may be way too late for your little one.
Send another question if you'd like advice on booking a plan that works for you, Amanda; I'd love to help!