I agree, as someone who has thought about buying in HHI that the 20 year marker is HUGE, when you see that value proposition, especially someone who may be vacationing for another 30-40 years (at least). Aulani, HHI, and Vero Beach are all EXACTLY the type of resort that we would want to be, with the possible exception of the fact we can't bring our dog, and he is without a doubt the most spoiled member of the household.
But, when I see the cost, even resale, and knowing I only have 20 years to use it, it just makes the math much harder to justify, especially when, in our case, the resorts we are looking at, aren't really that different from a Hyatt, Westin, etc. We only live 2 hours away from WDW, so an extended stay there doesn't make too much sense for us.
So in short, we really want to be DVC members, but I am not sure it is the best thing for us. Which makes me sad, despite it making sense.