I'd like to know this also. You guys are really helping me. I've never booked "hard to get" reservations, so I've never booked more than a week or so out. But our upcoming trip is an anniversary trip, so I really want a special one. These tips are helping.
Here is what I do. I make a list of all the reservations I want to get, and I put them in order of what's in highest demand. For our upcoming trip, we'll be trying to book Space220, Topolino Terrace, Storybook Dining, O'Hana, and possibly California Grill for a date night. There are a bunch of other ADR's we'll be looking to make as well, but the ones I mentioned are going to be the hardest to get out of what we have (loosely) planned. So the ones I just listed will go at the top of my list, the rest go at the bottom, and at 6am on ADR day I will go in order down that prioritized list in order to give myself the best chance of getting the reservation. I also try to keep the timing flexible for those days so I open myself up to a range of time slots.
We have an 11 night trip but it's a split stay, which means I can't book ADR's for the second leg of the trip until the 60 day mark opens up for that resort stay. We check out of resort A on Day 7, so I'm going to try for top reservations on Day 6 and 7: O'Hana on day 5, Topolino breakfast Day 6 or 7, Space220 Day 6, and Storybook Day 7. Cali Grill will fall during our second leg which means I'll be crossing my fingers for a reservation at 60+2 or 60+3, which could be a long shot. I'm hoping since it's just two of us and our timing is flexible we might luck out.
So on ADR day for our first leg, my list will probably be:
Space 220 (book for day 6)
Topolino (book for day 6)
Storybook Dining (book for day 7)
O'Hana (book for Day 5)
If I have success with all of those, then I'll move on to the rest of my list. If not, I'll try booking the backups we chose. Then when the 60 day mark opens up for the second part of our stay, I'll do the same for those days, with Cali Grill at the top of my list.