Possibly. But I do not think that's going to be a problem.
One advantage of being a DVC member & LIVING in Florida is that we are pretty flexible on our "Disney Time".
We NEVER plan an extended stay during peak times (Summer, X-mas, Thanksgiving, etc., etc..), and have never had difficulty getting what we want, where we want, even at the 7 month window for non-Home Resort stays.
I'm not so sure about this. The only reason I say this is because the Contemporary wings are the lowest priced deluxe rooms on property. I assume a portion of those rack rates pay for the CR monorail station.
If they can keep the rack rates low, than why not the annual fees?
I would say atleast 100. But like others have said I would need to see the points chart to make my final decision. I would definitly want enough for a full week's accomodations. I hope it happens.