The other thing I wrestle with is whether or not to wait until discounts come out to book. The arguments for doing this are: (1) you don't have to call to get the discount after you've already booked; and (2) by waiting, you sligthly increase your odds of getting a discount, as the resort occupancy will be sligthly lower.
However, the big argument for not waiting is that your desired room category in your desired resort may not be available (for that matter, your desired resort may be completely sold out).
Since we usually have our heart set on a certain resort, we usually don't wait to book until discounts come out (otherwise, we would).
So for us, it's usually the same drill. Watch and wait for rack rate online booking to be available, book online at rack rate, watch and wait for discounts to come out, and call to try to apply the discount.
Anyone else go through the same machinations?