So how does a person accurately calculate if this is worth it for them to make the move into buying
DVC?
If you can honestly answer yes to the following three questions, then DVC, purchased resale, can
potentially be a wise financial move:
1: Do you expect to go to WDW at least every other year for at least the following 10-15 years?
2: Do you normally stay in a mix of Moderate, Deluxe, and DVC resorts?
3: Would you rather gouge out an eye than stay offsite?
Note that resale DVC can only save you money on lodging. You will still have to get to Orlando, buy food, buy park tickets, etc. etc. etc. This is not an inexpesive vacation. (Yes, I know we can find other expensive vacations. That is not the point.)
If you can
also honestly answer yes to the next two questions, then DVC, purchased direct, might be "a good way to spend the money."
4: Do you have the cash on hand to pay for the points without financing?
5: Would it be okay if you got nothing back on your purchase when the time comes to get rid of it?
Note that answering yes to these questions does not make buying direct a wise financial decision. It makes it a good way to spend the money. To understand the difference, I'm going to quote a former Hyatt timeshare sales agent who hangs out on TUG:
It's a TOY. You are buying a TOY. Treat it like a TOY.
There is no universe in which buying from Disney is a wise financail decision, becasue something sort of kind of like it is available on the secondary market for fifty cents on the dollar, plus or minus. That doesn't mean you shouldn't buy from Disney. Buying from Disney is good and fun. And, because the thing you are buying from Disney is not exactly the same as the thing you could buy resale, you might decide that the thing-from-Disney is how you want to spend the tens of thousands of dollars it will cost, instead of spending those tens of thousands of dollars on something else.
What would cause someone to decide that? Simply that they want to. Nothing else is required.
Worried about "life" becoming less conducive to being able to take those week long stays going forward, or things such as jobs, health issues, or other life factors posing an issue to traveling, in the future.
This is wise, and was essentially the reason I
did not buy DVC when my kids were in the house. In hindsight, this was the decision for us, but not for the reasons I expected. I was worried they would age out of Disney before we got to the payoff horizon, and DVC would have been pretty much the only "big" vacation we could take for many years. I did not want us to be that limited. Aging out was not that big of a deal, but our lives evolved in many unexpected ways.
FYI, considering direct, since we love RR.
If you can answer yes to all five questions, then why not? I eventually did, and I am enjoying my toy so far. If you can answer yes to the first three, but not both of four and five, then you have a harder decision to make: Do you like Riviera enough for it to be your only WDW home, or would you rather have your home be among the non-restricted resorts?