After all the figuring is done, go with your heart. In my case it was BCV. Being able to book at 11 months is priceless. In the extremely rare case when I wanted somewhere else (Poly ), it was easy enough to get at 7months.
VGF better choice.
I'm an owner which I bought AKL at resale prior to the most recent changes in benefits for resale owners.
I recommend VGF. It is much more difficult to get a reservation at VGF at the 7-month window and that in itself adds value to your points. It also would be easier to rent out the points and at a higher price because of the premium location vs OKW. I am not sure but I believe OKW would be a much easier reservation at the 7-month window so there is a higher chance you would be able to stay at OKW even though you would have VGF points. And as to the maintenance fees, they all go up every year no matter which resort you buy into. LOL
Follow your heart, which, from your thread, seems to be screaming VGF (at least that's what I'm hearing). Buy where you want to stay and if you can afford VGF, go for it!! We're paying premium resale prices at BLT because we couldn't afford to add on there when it first opened and that's where we prefer to stay. SSR is our original resort and frankly, we just don't find the appeal there. The end date shouldn't be an issue; if your son doesn't want the points, he can sell them.
Non-Financial Financial Advice
I can't add too much to what has already been said, except to say I wish I had asked these questions last time we travelled to Disney World. So many thoughtful, creative perspectives. For us, owners at VGF and VGC, we just completed a trip to Disney World. We (my wife and I) split our time kind of like you are suggesting, three days in a 1BR at SSR and five days in a studio at GF. I also had some concerns about the formality of GF having spent a week there several years ago.
The advice I would take to heart is to follow your heart. We felt pretty remote at SSR, which felt more like a vacation condo than a Disney resort. From what I read in these parts, some folks prefer that feeling, but that's not us. We also enjoy dressing for dinner and going to California Grill for cocktails. But we saw tons of people at GF in super-causal attire, it seems completely within the culture of the Disney resort. We are grateful we own where we do because both of our home resorts are nearly impossible to book at the 7 month window.
Choose the fit for your personalities, and enjoy the ride!
My 2 cents
As a current VGF and BWV owner, my heart is with VGF over OKW for many of the reasons listed by other respondents - location, monorail, restaurants choices, etc.
My wife and I LOVE the atmosphere at VGF and never have we felt that we should be "more formal" - shorts and flip-flops work as well as jacket and tie. We've also found the 7 month window a challenge more so at VGF then at BWV.
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Bang for your buck for me
I'm a bang for your buck person. So I would buy SS, OKW, BLT in that order. We own at OKW and AK currently. I appreciate all of your points about both.
If you are a planner and have patience to be on a wait list I would go OKW or SS simply because I like more for my money, which if you decide on a given dollar amount to spend might give you the option to get 2 rooms when you become grandparents if you have more points.
While dues are a tiny bit cheaper at VGF, at current dues its a $1200 difference after 15 years.
Also a thing to consider which will make it more financially appealing is. You can buy double the points at OKW say 300 then rent half each year and it will pay the dues for all 300 points.
But always in reserve for you to use.
Good luck, I think you will love either place you pick.
If VGF is in the budget and if you like the resort, then definitely VGF.
We are typically best value people, so SSR was the best choice for us. However, if VGF was in the budget, then it would be no contest. One day we will have VGF points. Right now we have teenagers so we have no money . Once they get launched, (if not sooner) we will have some VGF points. Love, love, love VGF.
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