I've hesitated to comment as I'm not sure how much we're helping the OP at this point. That said, I offer a pair of thoughts which may be of use.
There is no reason to assume that the maintenance fees for VB will rise at the same rate as for the WDW resorts. From 2015-2018 VB increased 0.3% each year while SSR increases were in the 3.0-5.1% range. And it may just be that I've not heard about VB's tax situation, but the assessors clearly feel a substantial hike of WDW's valuation is achievable and are working toward that goal.
But the much bigger elephant in the room with all 2042 contracts is the question of what Disney will do and thus what value will they have moving forward. My impression is that Dean places a value of $0/pt on them in 2042 but I think that is exceedingly unlikely. The question then becomes how much residual value to place on WDW points and how much will that value vary by resort?
Will Disney offer an option to buy new points to existing owners?
Will they offer discounts and if so will they be a % or fixed $/pt?
Will they offer extensions of 15-20 years sometime between 2024 and 2029?
Will they seek to reduce or expand the number of non-WDW resorts?
Will they demolish any of the resorts?
All good questions.
IMO the long term prospect on the fees is they will rise as fast or faster simply because the resort has to be maintained no matter the rest of the economy though the last few years of any resort they should dwindle down but in a given year or 2 things will vary. I do place a value of zero at the end in Jan, 2042 and the limited experience with OKW combined with the failed sales project there makes it unlikely to be extended even if others are. But even if it is, it's doubtful to be in a manner that's financially feasible or that alters the issue at hand in favor of VB. They offered OKW at $15 ($25 with a discount) years ago and the real value at the time was around $7-8 per point by my calculations and that was born out by the sales prices of the 2057 contracts there vs the 2042 ones over the following few years. We simply don't know what will happen to the resort at the end, your guess as to what is as good as mine. However, I think it's DRAMATICALLY unlikely to be cheap enough to reduce the overall long term cost and extremely likely to increase the overall cost of ownership there looked at in the whole for anyone that participates. Disney has challenged the tax valuations and thus far has had some success doing so.
The variables at VB are different than WDW, esp OKW. The weather is a much larger risk not just for catastrophic issues but it doesn't have the transportation component.
The extension debacle is a whole different thread but what they clearly won't do is something that makes sense for the members as a no brainer or without taking a sizable chunk for themselves, it'll certainly be expensive comparatively so if they do offer an extension.
We could certainly have a similar discussion from a $$$ standpoint between SSR, OKW, AKV, etc and it's commonly done for AKV compared to SSR. The answer is the same financially as it is for VB unless one will buy less AKV points and use them for value rooms at least 2/3 of the times, that is the rough break even financially compared to buying SSR and using for standard view at AKV. But the dollar spread is less than the VB vs SSR and for WDW, they do the same thing save cost and the ability to guarantee a trip at 11 months out. There are also emotional components but they can't be qualified though they don't alter the math, they are just different. For someone that wants to stay at VB and WDW it can be a reasonable purchase. Before the increase to the 75 pt requirement to get perks, it was a reasonable option for that purpose in some cases.
BTW, the answer for HHI is exactly the same and the numbers are very similar.
