THIS. It is not an investment. I wouldn't buy with the expectation of ever getting a penny back. While it remains likely you will be able to recoup much of your initial buy-in if you resell, I wouldn't buy based on that expectation. I'd buy with the thought of: It is going to cost $XXXX, and am I going to get $XXXX of enjoyment out of the purchase?Wow, the thought process is very good. If you are thinking in the terms stated above maybe it is best you just bite the bullet and buy direct. Keep the points as long as it suits your lifestyle and when Disney trips are no longer a part of the plan, you can still sell them resale--maybe for a little loss but think of all the enjoyment received while they were owned. Lots of ways to approach the expense of DVC. Everyone is different with their own wants, needs, and expectations. The only thing I advise is to NEVER consider the purchase of DVC as an investment, it is a Time Share and should be treated as a Time Share.
I bought Riviera direct. I'm not particularly young, my kids are teens. It is highly highly unlikely that I'll personally keep and use the contract for another 50 years. But my plan is to pass it to the kids, they should be able to take nice trips with only paying the annual maintenance. Maybe I will re-sell it before then. Maybe they won't care for it and they will re-sell it.
The only guarantee I would look at with re-sale: You will get out of paying annual dues.
If we (me and my wife, later my kids) keep it for the full 50 years - it will obviously be worthless by then. But we will have gotten generations of good use. If we re-sell it in 15 years, even if it's nearly worthless, I expect we will have at least gotten good value over the 15 years.
As to buying direct or re-sale... that's an equation that involves more than just blue card perk math. But it's quite clear that with future re-sale restrictions, in the long term, direct will be more valuable than re-sale.
The issue now is that for many people, there isn't a huge difference between direct and re-sale. If you don't care about the blue card perks, what really is the difference between buying Riviera direct and buying Bay Lake Tower re-sale, for example. The only structural differences are 40 year contract vs 50 year, and privileges at 14/15 resorts vs 15/15. But 15+ years from now, there will be far more significant structural differences. And 25 years from now, re-sale will likely be basically just home resort use while direct will be all-resort, really stretching the value difference. (on a side note, the structural difference will be so big, I suspect they will get rid of many/most/all blue card perks).