The Chinese proverb is that the best time to plant a tree was 20 years ago; the second best time is now. For current owners (today), all of this is somewhat academic regarding our use of the membership; we're grandfathered.
I'm STILL not convinced that buying a 75 point contract to mitigate the restrictions is worth it, but I already have all of those things built into at least one of my contracts. Put another way, the point of the restrictions is to get buyers to throw their hands up in despair and buy direct. To the extent that becomes the case for new buyers, there's another option, a cheaper option. I'm just trying to lay that out in the purchase forum so that potential new buyers after this week have something more to consider, IF it's important to them.
Surely, you could also make this work by buying both the resale and direct component at the same resort/use year. I think that the added element to the equation for the L14 is how it will affect their values going forward. Today, the values are almost all based on "location, location, location". Going forward, the end date is going to become a bigger factor because of this restructuring, so hedging end dates would seem to be a good idea.
(Unlike the previous changes, this change is going to make current owners really pause before selling. Once they sell, even if they buy back in a few years later, they cannot get back what they will lose. I think that also is going to have a decent affect on values going forward.)
So far as the risk to maintaining multiple 11 month windows, I might be blind to that risk as I routinely juggle three different resorts. To me, the biggest risk is that it increases the possibility of split stays, which doesn't bother me at all but my wife's mileage varies significantly on that one.
I don't think that 
DVC is interested in extending the 2042 resorts like they did OKW, but some extensions I believe will be necessary. It won't be healthy for the system to take several resorts out at one time, and it won't be practical to rebuild several resorts for selling new all at once. They are going to want to stagger that out over about 2-3 years per resort. I could see them offering 2-8 year extensions just to stagger out the rebuilding process. I'm also not sure that they'll keep VH and HHI in the system after 2042.