Flights, it's a toss up. We are leaving in 29 days, I watched the cost of flights and rental cars daily, I first looked at the airline that we use, Delta, and then looked for the flight that we wanted, normally, the earliest available on the day of departure, as we are morning people, but then who isn't when heading to WDW!!
I found the flight, and a price that I thought we could live with, at $208 per person, watched it daily, saw that the cost of that particular flight went down $40, until about a week ago and then the price SKYROCKTED!!!
My advice is pick your flight, when it gets to a comfortable price for you, book it and DON'T look at it again!! You'll know that you have your flight secured, and that's one little piece of the puzzle in place!!
If you're booking a rental car, I'd wait on that until the last minute as the price most likely will drop and you can save a little on that.
Good luck!