When you said the followingI was not insinuating that you would get anything different buying from DVD in regards to contract length even though there is that oddity with 2057 OKW contracts direct. What I'm saying is that you have the option to buy contracts with about 25 years on them for half the cost per point through resale versus what you'd be paying for a resale contract ending in 2042. I thought this was more clear since the OP was referencing Wilderness Lodge, which has two DVC options. Direct you will get roughly 49 years at $182 a point whereas resale you will get roughly 24 years at ~$90 a point. To me as a potential buyer I would wonder what I'm getting for the additional risk and slightly higher maintenance fees, which is why they dangle the perk/discount carrot to make sure people know they will be considered second class citizens if they take the cheaper option.
[edited to add original quote]
"I think given how steadily they have been increasing costs they have to dangle a carrot in order to give people a reason to buy through them when they might get half the contract length for half the price elsewhere "
I thought you were comparing apples to apples. In other words, a direct contract at XYA resort to a resale contract at XYZ resort. Not as you said above - a "new" direct contact - Wilderness Lodge Cabins (or whatever they are calling them) as compared to a resale "old" contract - Original Wilderness Lodge.