Which is more important to you, the specific resort/room/view you're unable to book, or the dates you want to book?
For us, the dates of the vacation are always the most important aspect. I need to lock in vacation days early at work, and always want to book our flights as far out as possible to get the cheapest Southwest fares. For those reasons, I'd personally look for the room size I need at another resort (or with a different view) and book that, today. At the same time, I'd waitlist the entire stay for the resort/room/view I really wanted.
SSR is my favorite resort, so that's where I'll usually book a "stand-by" reservation if I'm going for a last-minute reservation inside the 7-month window. It's large enough that there's usually availability, and with the exception of OKW, the rooms are usually fewer points than the same sized room at other resorts. So when booking at SSR, I know I won't have borrowed too many points when (if) I cancel and re-book at another resort. And if the waitlist doesn't come through, shucks, I get to stay at my favorite resort.