tl; dr - DH and I both had (have) jobs that require advance planning to take a vacation. Before having kids (and we had kids quite late in our marriage), we'd just tag along on each others' work conferences, tacking on a long weekend before or after, and call it a vacation. This worked great except for the part where we got used to subsidized flights and upgraded/luxury accommodations...
I grew up going to WDW and DL as a kid in the 1970s and this was me...
I remember my first WDW trip where I was on the ferry coming to MK for the first time, being 9 or so, and looking across at VGF and wondered what you had to do to stay at one of those. Our trips were always very low budget, off-site, with my dad doing crazy things to save a couple bucks (two layovers? Yes. The cheapest vrbo? Check. Off site questionable rental car agency? Also yes. ). Within a few years of that my family who we traveled with bought DVC and I was still jealous of the niceness and convenience of their trips
The DVC seed was planted there.
... except the Grand Floridian hadn't been built yet, so we would take the monorail through the contemporary. VRBO didn't exist, but my parents did get the all "suite/efficiency units" that were a 20 minute drive from WDW, and it was like driving through Kansas farmland and then landing in Oz when we got onto WDW property.
In order to afford DVC without financing, DH and I put a lot of time and effort into our careers, and put off having kids for a long time.
Even so, old frugal habits die hard. Before kids, we did a few cash stay offsite (hotels with the phone bolted to the end table, that made value WDW lodging look luxe), and onsite that were usually finding last-minute travel deals. While our kids were young and my parents were both with us, we did a few Disney trips at offsite timeshares (w my mom), and also a few Swan/Dolphin stays. Then we dipped a toe into renting, and I probably could have done that for a long time (back when rental rates through this board were $12-13/pp, those were the days!!). We stayed in a 2br at BLT with extended family at the beginning of my mom's long illness, and I saw the value of us all being in one large unit or close together.
Not long after that, rental prices went up and up, and Starwood merged with/into Marriott (and the points conversation wasn't so great). Also, we did appreciate not being in 1 hotel room with the kids. Because old frugal habits die hard, I know I never would have spent the cash to pay for a 1br or larger suite, but somehow I could do it if I were only spending "points" - and we do sometimes still stay all 4 of us in a studio (my kids are 11 and 7 now).
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We added on several times, and now have 3 home resorts (BLT, VGF, RIV), but these are some of the more granular reasons why we bought DVC:
2. Location - you mention AKV/SSR so maybe this isn't important to you, but we wanted access to resorts neighboring parks, and other than swan/dolphin, you aren't going to stay in a park area without a stiff cash outlay. I know occasionally you can find good deals and packages, but the price per night at the contemporary or poly feels a lot worse than the points/dues costs. I know those rooms are higher points than an SSR, so it's all a cost analysis for what you may plan to buy.
BLT because of those monorail rides through the Contemporary when I was a kid. Also because at the time we bought, it was the only one that had a walking path to MK. Until recently, MK was our kids' favorite park, and we often took trips that avoided HS entirely. A lot of that has changed, which is part of why we bought RIV.
3. Motivation to travel - I like others on the board work a job where I could (and have) fall into the pit of not traveling if I don't have something booked. The booking windows personally help me make sure I'm taking the time to plan something.
Yes. And it starts the conversations with family and friends about thinking about dates/times we could make a trip happen. I have young nieces and nephews now, my dad, now a long-retired widower, has lots of flexibility, and I like that I can treat him to a Disney vacation with my kids. Last summer we were in a 2br and a studio at BCV and I am forever grateful to the CMs who put us in rooms across the hall. It was magical.
4. The ability to stay in 1/2br rooms truly changes the way we travel, and that's the big perk to us of DVC perhaps above all others. I simply would never pay cash for that type of room, maybe that's a mental block, but especially with a small kid, the larger villas were a big plus, and funny enough, one we thought we wouldn't care about (we laughed off a direct guide when he talked about this to us). The ability to stock up a fridge, do laundry, sleep in separate rooms, etc, just took so much stress out of our trips. We were the prototypical "we need more points" after our first 1br stay.
^^^ this was us also. I think we bought more points before we finished up our "let's rent for a few trips to decide on a home resort" plan and were already considering more points after our first points stay. (this is what happens when you buy a loaded contract- beware!)
Timeshare changes the way most people think about vacation. It doesn't make sense to use timeshare assets for much of anything other than vacation, and the use-it-or-lose-it nature of those assets tends to move vacations higher up the to-do list. And, to me, that's the real value of a timeshare: it encourages you to prioritize vacations.
I've owned timeshares for close to 15 years at this point, and am now up to five weeks (which, frankly, is probably at least one week too many). There is no way in the world I'd be taking as many vacations as I take now if I had to justify paying cash for each of them individually. But, the money I am spending is discretionary cash I can afford, and looking back on it, it's hard to imagine any better use for it.
So, yes, you might save money buying DVC. But, maybe that's not the reason to buy DVC.
Agree 100%. If we didn't get DVC, we'd be putting together last minute trips during school breaks, which is not exactly the best financial plan either. For this upcoming April break, we had originally booked a WDW stay (in case the older child's band group ended up going), then we thought we were going to CA to visit family and stay at VGC (we actually booked a rom at 7 mo) before changing our minds once again and modifying our stay to AUL. I do the vacation planning for the family - there is no way I would have done this if every trip involved researching and planning each now location. (And if my cancellation at 5-6 mo out helped you get your VGC room, you're welcome!
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We are now staying in an ocean view 1br at AUL - it's not available as a cash reservation, but the limited comparable hotel rooms at AUL and other resorts are around $1000/nt. We are having a vastly different experience than if I were to pay cash - which would have involved renting a vrbo that was a drive from the beach etc etc etc .... I mean, yes I'm sort of saving money, but not, but I am having a much more luxe vacation than I ordinarily would pay for.
(My parents had a regular style timeshare (RCI?) and we did get Hawaii condos but they were nowhere near as nice, and I remember my mom stalking and calling and writing (no internet) 12-13 months in advance. For all I know she was doing the old school version of walking a reservation.)
I have a question about using DVC points to use for other timeshare vacations. My understanding is that it is not the best use of points but in my situation a big reason I am buying is to ultimately pass it to my daughter for her use. Once it is hers with the obligation to only pay maintenance fees (with money left to her) getting the most efficient use would be great but is there enough value in using points in the timeshare market to see that as a decent benefit?
Would the value be worth at least the maintenance fee?
I think that is our plan with our kids too, to leave the contracts to them and with some $ to pay the maintenance fees. As for using the points elsewhere, we explored doing this with resale contracts we bought with expiring points, and always ended up deciding to rent out those points instead, and use the money elsewhere. I know Disney touts that as a benefit, but it's been pretty easy to rent out the points and just use that money toward travel.
Is the Swan/Dolphin room price significantly higher for the equivalent of a 1 or 2 bedroom?
Do they even have the equivalent room style?
in short, no - the suites we have looked at don't usually sleep the additional people in the living room, if at all. There is also no kitchen or laundry. So it's not really equivalent. I was looking at Swolphin rates recently and they seem to be very high. Pre-pandemic it was pretty easy to find rooms under $300 and sometimes under $200. We have a lot of Marriott points, so we've stayed there with the kids and had some great views. But at best - Swan hotel rooms are 2Q beds in a hotel room that has, at most 2 sinks, 1 toilet and a shower tub combo. the layout with the bathroom made it hard for more than 2 people to use the space at the same time.
I think this time I may actually jump in because I see this as an investment - in ME. WDW truly is my happy place. It's where I go on happy days and sad days, and I can spend the day without going on a single ride and feel all my stress drain away. I've even been stuck working through half my Disney vacation but knowing at the end of the day, I can still get in 4-6 park hours still made the day end on a high note. It's been 7 weeks since my last trip and I feel it. It's so easy to cancel a park reservation if something comes up, but having a stay? I think I might actually take more of my PTO!
I keep looking for the downside, but I haven't found it yet, despite pouring over just about every thread there is. I guess I just need to find the right contract now! Actually two, despite everything about 2042, I have a very emotional attachment to the Crescent Lake area so maybe just a small one for the 11 month guarantee.
I think this encapsulates my feelings about DVC now - no doubt things have changed a lot since we bought in 2017, since we were renting and staying at Swan/Dolphin in 2013 - 2017, but so have our priorities. I'm really feeling like time with our kids is even more precious than before. During the pandemic, Disney was my happy escape. While it may not feel quite as magical as it did when the kids were tiny little, it's still our place for happy family time. Even though we do go to other places for vacation, my kids still love going and DH and I enjoy things beyond the parks now too.
(he does get to reap the benefits of going with) 
