You probably have figured it out already, but in case you hadn't...if you alternate banking points between the two resorts, you would have 200 points to spend each year at one resort, and you will have the 11 month booking advantage. It would be fairly easy to manage, esp if the uy were the same. The first year one would only have 100 points though..
I think having two contracts at ones two favorite resorts would be the way to go.. imagine, no waitlisting, no switching ressies..
There would also be some cons to this though. If you couldn't go one year, the banked points are at risk so one would have to use them. Should be easy to rent though, they can't be banked again or transferred to another member.
More than you wanted to know I am sure.. good luck.