I would book... but don't add
travel insurance. If a promo comes up or you get a pin... it can always be applied...or you can change dates. I think the only thing that complicates things is if you try and cancel and have travel insurance. Course.. I think then it is only that you don't get that part refunded.
I booked my December trip right after Christmas. I had a pin that gave 40% off deluxe rooms.. and WL doesn't have a ton of standard rooms. I am sure they fill up fast (if they haven't already) I figured it would be best to book asap..and if a better discount came out I would apply it. I ended up changing my dates... and so I am still watching for a good promo to apply to the added days. You better believe if I see one come through I will be on the phone modifying my reservation.