If buying resale and going with the original, nonrestricted resorts, yes, the maintenance fees are a definite consideration, but given that you're flying from overseas and probably doing a longer stretch of vacation, I kind of would hate for you to count on 7-month availability for a 7-14-day trip in one location. I am very much in the buy-where-you-want-to-stay camp. If you ARE planning longer trips, always book your home resort to lock in a place to stay as a safety net, but you can book it in chunks, like days 1-7 home resort to get settled and relax and enjoy everything at the resort. Days 7-10 at the next resort near Epcot to take advantage of Monday nights DVC Extra Magic Hours, or whatever they call it. Days 10-14 at a MK resort to take advantage of Wednesday night DVC Extra Magic Hours (so long as your trip isn't August-December, but you said February is what you're thinking of.)
What you do is book your home resort, and at 7 months try switching/waitlisting each of the second and third chunks for a MK/EP area resort. If you get it, great, but if not, call Member Services and they'll just rebook the whole shebang under one reservation number so you don't have to move rooms within the same resort.
AK has higher dues, but they also have club level (only DVC to offer that.) It's at Jambo, and our friends who own there grabbed it once and LOVED it. Since you're looking at a few years possibly of empty nester trips, you may LOVE having "free" food on site and relaxing looking at the savanna. There's also value rooms there, but those seem to be grabbed by walkers from what I hear, so you'll have to investigate that further if it's something you want.
As well, Kidani is about to start its refurbishment this fall, and Jambo is getting refurbished starting next spring, I believe. AK contracts are very reasonably priced and plentiful, which is nice for getting your feet wet looking at contracts.
Regarding the potential makeup of your parties, Kidani and BLT (and now the Poly Island Tower -- PIT,) are the only resorts with an extra bathroom. As a family of five, almost all adults and potentially bringing friends/partners in the coming years, that's a great benefit.
My son and I just did AKJ this past January and loved it. Your points go very far at the resort, so you don't have to buy as many, and we found the buses ran constantly and were timely. Yes, it would be great to have a Skyliner or Monorail or boats, too, but AKJ/AKK is really a relaxing world unto itself, and the food on site in all categories is excellent.
BLT just had an awesome refurbishment, and that's MK access. If you prefer MK as your park of choice or like the holiday parties, that's a good option. Some of the views I hear can be hard to grab if you don't own there, but IDK much about availability. Dues are low, and if you wanted to keep DVC for potential grandchildren, walking out of MK after fireworks can't be beat.
VGF has low dues but a high
point chart, as does PIT. So again, you pay less in dues but need more points to grab the 1B/2B. Demand around the holidays is very high, so you would want to own there if that's a priority for you.
OKW we love. If you can find an extended 2057 for sale, I don't think you'd be sorry. If you ever want a 3B grand villa, it can be tricky to nab one, so having home resort advantage may be good there, but otherwise you can get in there pretty easily. Dues are higher, but if you rented a car, you can park right outside the door.
SS is everyone's sleep-around points (SAP) choice for low dues, but it always has availability, so I hate to kind of waste home-resort booking on something that's always available. Your older kids (and you, as a couple,) may love just walking over to Disney Springs for music, dining, shopping, and nightlife though.
Copper Creek (CC) is reasonable dues and pricing. It's on the smaller side of options, and apparently it's a knife fight to get rooms during the holidays for every room category, but the theming is gorgeous there, pools are good, and if that aesthetic speaks to you, it's really peaceful and beautiful all year round.
BW, BC, BR are all 2042 resorts, so up to you if you WANT the contract and dues to be ending then so you don't have to continue paying on it. BW/BC are very desired resorts and hard to get into more than a day or two at a time if you don't own there. They each were just refurbished and spruced up. BW/BC are definitely booked up for F&W and every RunDisney event week, so just keep those dates in mind if you're trying to swap in at 7 months at either of those.
Our kids are now almost 12 and 13, bought in at 5 and 6. DD is still gung-ho on Disney, DS is meh and usually wants to chill in the room and loves the pools and water parks, which is fine. Our solo trips this year, me and each kid separately, were really great. They're both good traveling companions.
I don't know too many folks who would turn down a free WDW trip, but they're out there. We have brought my sister, BIL, and niece twice now in a 2B and loved it. Plenty of room (we like dedicated 2B so we can hang out together for meals.) We provide the room and split groceries. They always treat us to a fancy meal and have given is a hefty Disney gift card, which is not necessary at all, but I appreciate the appreciation! LOL.
Regarding bringing the kids as they get older and who pays for what, I anticipate paying for the kids' airfare and tickets and whatever meals we do in the room, but any restaurants/QS/souvenirs would be on them -- at least until they're done with school and/or settled with a job.
My parents were BROKE their entire marriage, and if it wasn't for my grandparents paying for a beach cottage and treating for one big family breakfast during the week, we never would have been able to go anywhere as kids. So, my perspective is I'd rather pay and have them be able to go versus not going while my husband and I are still mobile and able to do things with them. At some point we'll be physically limited, and right now we're not (DH needs a
scooter though already.) I want to make memories now for when I'm too old to do things later, and if it means paying for airfare and tickets but we cook in the room almost all our meals, so be it.
To be clear, I will not be doing all the cooking of meals in the room, LOL. Momma needs a break, too.