I am looking to go to the World some time in September 2016. I am hoping to take advantage of free dining, if it is offered again, and was wondering when is the best time to book. Now? A year out from when I want to go? or should I wait until 2016 when/if free dining is announced? I think prices change every August, so is it wise to book before then to lock in on this year's price, vs. waiting and paying next year for the inevitable increase? Thanks in advance
You can book room only 399 days in advance.
I recommend that if people are planning far ahead to book around 9-10 months (latest) in advance. This is so that you can make your dining reservations (ADRS) 180 days out.
Then, if any promotions or discounts come out, you can call and have them applied if your dates are eligible. You can do this yourself or if you book through a good TA, they can do handle all this for you. Sometimes when the promos come out, people have been on hold for hours. A TA can help with that.
There's a list of Liner TA's if you do a search on the forum. I created a thread with the link to the list.