Just thought of something, I'm not sure how often you intend to stay at VWL vs. SSR. Some people bank and borrow on that particular contract, so that they have either 100(for a stay every other year)or 150 (for a stay every third year). You can always book at SSR and then try to change at the 7 month window, or book what you can of the weeknights at VWL ,then book the weekends at the 7 month window(Generally easier to book). It will just depend on what time of year we are talking about. I think the other folks have anwered your cash questions, so I'll leave that to people who have more experience.