We're going in September, and when I called a few weeks ago for reservations, I was surprised at how many of our first choices were already booked on the nights we wanted them!
I've been to WDW before, but I've always just eaten whatever was close by and cheap, which usually meant counter service for almost every meal. My experience is that this way allows maximum flexibility, but it also tends to leave you with a fast-food-filled vacation. Bleah!
This time, we're doing the dining plan, so I want to take advantage of the opportunity to eat in nice restaurants! So here's what I did: I went to several WDW websites and read the restaurant reviews. Based on the reviews and our own personal tastes, I chose at least one table service restaurant that we want to try in each park. (I'm not counting AK, because there are no table service restaurants there.) I chose more than one if there was more than one option that sounded very appealing.
Then I made a very, very tentative schedule of one way we
might spend our time. I guessed at how many days we'd want to spend in each park and which days we might want to be here. (Understand, none of this is in stone; it's just a rough estimate.) Based on that, I assigned each of the food options to a different night.
I called and made my reservations, changing things around as necessary to fit what was available.
Then I threw away the park schedule I'd made, keeping only my restaurant reservations. This way, we're free to do whatever we want to do based on crowds and random whims, and the only thing we have to keep in mind is where our daily table reservation is. If we decide we're having too much fun elsewhere, we can just skip it. Otherwise, we have a guaranteed spot. It's win-win.
I hope this helps!
-p.b.