What is the advantage to waiting for discounts? I'm still new to this planning stuff, so forgive me. I was under the impression that if you booked and a discount became available during your planned stay, you could have the discount applied. Is that not correct?
You can, but there are a few camps of thought on this matter (well and several variations...):
1) Disney looks at the currently booked rooms when deciding on discounts and releases room based on the remaining availability. If you are already booked into a room, it decreases the likelihood that your room category will be released at a discount. You can then switch to a different room to get a discount, but it seems that your original room will then be placed back into rack rate availability, which doesn't allow anyone else get your room at a discount either. This camp thinks that if everyone who wanted a discount waited until they were released before booking, the pool of rooms available at a discount would be greater, which would allow more people to get the discounts.
2) You should book the room category that you can live with without a discount, so you have something acceptable in the event that no discounts are released and everything gets booked.
3) It doesn't matter because Disney anticipates people altering their reservations when discounts are released, and takes that into consideration when releasing the discounts.
Ultimately, if you book now, you may very well keep yourself from getting a discount in the future. It really depends on what is the most important to you: a good deal or a particular room category. Obviously, it's very difficult to predict what Disney is going to offer in the future, so do whatever you feel comfortable with. The only reason I'll probably book a placeholder reservation in the future is in order to utilize the 180+10 for dining reservations. A discount is the most important thing to me, so it doesn't make much sense for me to get my heart set on a particular category, when there's no guarantee that I'll end up there.