I'll expand on my thoughts and try to actually make SOME sense along the way.
Let's go back to 2001 and look at how SSR came to be. Originally Eagle Pines got the green light. Then the impact of 9/11 began to set-in. Disney decided to close the Disney Institute and SSR became an answer to two problems--new DVC resort and use for DI property.
Wouldn't the same logic apply to the Contemporary? The SSR Phase 3 decision would have been made 18-24 months ago. Tourism was still well below pre-9/11 numbers and the resort was throwing money away trying to maintain and service those rooms, when the guest population could easily be shifted elsewhere. The Garden Wings at the CR have been in disrepair for years.
I keep getting the sense (my perception only) that the longer this drags-out and the less likely it is to happen. In the face of higher tourism and a well-received remodel of the CR rooms, why would Disney want to turn this prime real estate over to DVC?
There is a precedent of additional construction at OKW which occurred after the Boardwalk.
Two other factors to consider:
1. I've read many times how people thing SSR is "too big", "pool is too small", and other related comments. These perceptions have to be impacting sales on some level. If the orignal plan for 550 units had been maintained, these fears would have never been an issue for current and prospective owners.
2. Sales of the "Phase 3" units at SSR would have received a boost if it occurred AFTER the Contemporary were part of DVC. DVC sells the entire resort package as a whole, regardless of where one owns. The CR would undoubtedly add value to all subsequent sales.