How would you do this?

Cash stays may be similar or lower in cost to owning DVC at the Cabins at Fort Wilderness, which you said were a favorite. In this post linked below, Patmcpsu said that cash rates for annual pass holders were $294/nt for Aug 18-21. That same period if using points would be 20 points a night. If you valued points at $20/each that would be equal to $400/nt with using points.

Given your situation with retirement looming and not really wanting to pass on DVC to your child, I'd recommend cash stays using discounts or renting DVC stays if that ends up cheaper than cash stays booked through Disney.

https://www.disboards.com/threads/cfw-at-7-months.3971364/post-66292930

Maybe play around with the Disney website for stays at CFW and look at the points costs with the points charts.
 
It is only one component to the visit... I'd also point out that DVC even on studios compares negatively to cash rates at the All Stars in a lot of instances. 1 BR units at some resorts can, at times of the year not even compare favorably to owning vs paying disney cash rates after discounts.

DVC can help somewhat with the dining aspect, and it appears to me that Disney dining is seeing demand softening (thus the Dining Plan promotion in 2026 for example - and the inclusion of DVC members in said promotion).

Don't even forget the cost of park admission! Whether it is an AP or a day ticket, they are expensive to get into!
The per day cost doesn’t seem worth it to me unless I have at least a 5 or 6 day ticket.


There are two ways to approach that. Go less often, or go less expensively.

We just got back from a long weekend, where the extra spending was targeted. The Party tickets were the "big splurge." We skippted the rental car I'd normally get. I had originally planned several pricy sit-down meals, but we scaled back once we were there.
Yea, I always make 2 or 3 dining reservations per day, but definitely ALWAYS cancel one or two each day if not all, you just never know what you’ll feel like 60 days later.
 
This is the part of your question that stands out to me. DVC can (maybe) save you on your WDW lodging costs, but it doesn't help *at all* with tickets, food, transportation, etc. So, even if lodging were completely free, could you comfortably afford regular WDW visits once you are in retirement?

If it were me, I'd probably focus on doing what I could to fund my retirement before thinking about spending high-four-to-low-five-figures on DVC. This is an unpleasant answer, but it might also be the most important thing you can do right now for you and your son.
I've come to the same conclusion. The reason that I booked this trip and I'm doing it the way I really want to do it (cabins, golf cart, dining, eight days) is because it's 60 I feel like me being able to do the Parks the way I would want to is going to be fading. And since there's really nobody else in my family that is as into Disney as I am except my son, and he is autistic, it just doesn't make any sense. But I can live vicariously through others.

I think I'm really going to cherish this trip that I'm taking with my son Charlie. It's our dream trip.
 
I've come to the same conclusion. The reason that I booked this trip and I'm doing it the way I really want to do it (cabins, golf cart, dining, eight days) is because it's 60 I feel like me being able to do the Parks the way I would want to is going to be fading. And since there's really nobody else in my family that is as into Disney as I am except my son, and he is autistic, it just doesn't make any sense. But I can live vicariously through others.

I think I'm really going to cherish this trip that I'm taking with my son Charlie. It's our dream trip.
After you go on the trip let us know if you're a member 🤣
 















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