There are no absolutes when it comes to waitlist success. It's all about the specifics (popularity of dates, popularity of resort, size of villa being sought, how long you wait to get onto the waitlist, etc.)
November features the Food & Wine Fest, Food & Wine half marathon and "Jersey Week", just to name a few events that can bump demand.
Every waitlist success story starts with a cancellation. And the room goes to the first person on the waitlist. Sadly there's no way of knowing how many others are waitlisted for the same dates/resort/room size, nor how many cancellations will occur.