Resale market inventories are quickly increasing.

This will be interesting to watch.  Presumably this has already started.  Let's say OKW is $100 now (ballpark).  That's down from prior years right?  If there are 20 years left on it then we can say it will lose an average of $5 per year.  It'll probably lose a little less than that per year in the next few years then a little more in the later years.

Now I believe the valuable resorts will have a drastically different experience.  Look at the Starcruiser - as soon as you say it's closing, it books up instantly at full price.  Same will happen with Boardwalk / Beach Club.  You know if and when these get reimagined after 2042 they'll have a vastly different point chart, like Riviera high.  As we get closer to the end, people will realize their time to stay in these prime resorts as we know them will come to an end, and they will be as hotly demanded as ever for the cheap chart and prime location.  This uber demand will prop these resorts value heavily right up to the last few years because owners hold the cards on getting these rooms.

We bought in cuz I think it's going to get progressively harder to trade into the Boardwalk in these waning 20 years.

Another interesting math problem is what will happen to booking at what remains of the valuable resorts after 2042.  Losing two of the prime resorts BW and BC, will this mean other prime locations like BLT, Poly, GF get more demand?  BW & BC are about 8,000,000 points... but OKW, BR, HH, VB (non-prime locations) are about 11,000,000 points (taking OKW at a guess of 80% non extended). 

So in 2042 we'll take 11 million non-prime resort points out of the system, but only 8 million prime resort points.  I think this will be overall a good thing for those who still own after that.

OKW cannot be accounted into this. While some deeds end, the resort does not - the entire end year of the resort is 2057

Is there any possibility there will be offers for extensions? I think around 2032 there will be a rapid decline in value with those 2042 properties. It will be very interesting to watch this whole scenario unfold.

But you can't make the assumption that rental rates will remain the same. As MFs go up, surely rental rates will go up.
Also, isn't the idea of "resale prices crashing" based on the assumption that a person would say "I own, but I could rent cheaper, so I am going to sell and just rent instead"? If that happens, the rental demand would increase, leading to an increase in cost of renting, which would counteract the idea of it being cheaper to rent.

It is obvious, though, that if it was the year 2038 and there were four years left on a contract, it wouldn't sell for much on the resale market. Except maybe the cost of four-year's worth of trips maybe. And if we paid rack rates for the two-week 1-bd OKW trips we take, I don't even want to know how much that would cost.

Except suffice to say, if we had to pay rack rates....we wouldn't be going for two weeks in a 1-bd. Which is pretty much why we bought in the first place.

If there are less years left you might need to figure in closing costs when buying and agent fees when selling

Yeah I am aware of that debacle. But that doesn’t mean there may not be some other extension proposal. Never say never.