Hi Garrett!
Personally, I like to book my trips as soon as I know the dates I'd like to travel. This allows me to maximum flexibility in booking the room and resort I want without worrying if it will sell out. There really isn't a downside to booking early.
If you book early, and then happen to see that a discount is announced later, it shouldn't be a problem. Disney reservationists are almost always able to apply a
newly announced discount or promotion to an existing reservation. As
long as the resort and room type you are interested in is available, you
shouldn't have a problem applying the discount. If your first choice
resort is unavailable for some reason, you are usually given an option
to change rooms or resorts- most often without a charge.
To find the best deals, keep an eye on the
Special Offers
page of Disneyworld.com and be sure to call 407-939-7675 (or contact
your travel agent) if you see a new discount announced. Just let them
know that you'd like to apply it to your reservation when you call.
Hope you end up with a great deal on your vacation!
Good luck planning and be sure to let the Moms Panel know if we can help with any of the details!