September has been really easy to get what we want (not Labor Day). May has been harder for the Epcot resorts. We own points at both BCV and VWL.
I booked at the 7 month window for May this year for the Epcot area and I couldn't get BCV, but I did manage to snag Boardwalk (standard view no less - weird, huh?). I think May having the flower celebration at Epcot makes it a little harder. And then the BCV being smaller than Boardwalk makes it harder to book, thus the reason why we bought points at BCV!
January after New Years is over has been easy to get what we want also.
We usually travel in September, January, and May. May has been the hardest one to snag, especially for BCV when we have waited to book and lost our home resort advantage.