I certainly would and have.
Some here think of DVC as buying it for the next generation and passing it down.
Some here think of DVC as retaining value that they can sell later on.
I think of it as locking in roughly half the cost of future vacations now. The more years of vacations you want to partially pre-buy (annual dues make up the other part), the more it costs.
There are different quality locations and quality levels you can buy, and for different durations at various price points.
It's really hard to predict out 18 years to see what your family would want.
I would impute a cost of each vacation (using a time value of money to discount future vacations) and decide if pre-buying that type of vacation for that time period is worth it to you.
A Grand Floridian cash booking will cost more than an Old Key West cash booking. The same thing applies for pricing a VGF contract vs. an OKW contract. And 2042 vs. 2057 - the OKW differentials are fairly representative of the time value of money differences between the two - you simply can't divide by years. Roughly $1 a contact year is a good rule of thumb.
I think the 2042s are generally a good value vs. the longer contracts. The fear of the expiry, the dividing by years math the direct guides use, all overestimate the value of the larger contracts.
I don't think you're entirely off base here, especially when you consider the points premium difference...
So, OKW costs about 262 points for a 2 BR in February. Let's say you buy resale at $80 pp - your sunk cost is $20,960
VGF costs about 410 points for a 2 BR in February. Let's say you buy resale at $160 pp - your sunk cost is $65,600
From now until 2042, you have a decent, if not great shot of being able to use those OKW points at VGF - especially if you book early. And your dues go away in 2042... OKW becomes worthless at that point, and VGF will likely have some value being it is a flagship, monorail resort with walking path to magic kingdom... but who knows... MK could close and you're stuck with this dopey hotel building in the middle of nowhere with no swimming pools! Could happen!
The only disadvantage is remembering that you are in fact an owner at Disney's Old Key West... and that the dues are higher, and will continue to go up and be compounding off a higher number. Also, the structure of OKW as a resort means I believe you are likely to have higher dues than VGF which means the growth rate may continue to be higher at OKW than VGF.
To me, VGF and OKW also show so well the difference between levels of DVC products. OKW is a great value play for ownership in my view. VGF is a luxury product in my view.
Personally I struggle with the math with some of the other resorts.... I'd buy VB at around $25 a point, HH around $35... I'd rather buy CC than BR because the
points charts are similar and the price differential isn't as severe as the math above. I can't wrap my head around buying BW or BC... I'd trade into them, but can't see actually buying as much as I might be tempted as the BW is my favorite part of WDW...
Did I just persuade myself to sell my VGF contracts and buy OKW?