@intamin - I really liked your point that the main reason was for bigger trips to WDW over the winter holidays. If OP is mainly focused on WDW then it makes a lot of sense to start with resale at WDW at a home resort that you think you would enjoy over the holidays with your extended and/or growing family. With the exception of Riviera resale (which I'd never advise as a "first"
DVC purchase), any WDW points are usable at VGC and you could still try it out if you happen to see availability. It is possible - I have booked 1br/2br at VGC in April and December with WDW points. I just wouldn't expect to be able to get rooms, and treat it as very lucky if you could. (and you could rent points if you really really wanted). Either of the DL DVCs are a big outlay of $$$ for a first-timer who plans to use the points mostly at WDW.
I love this - I also bought an initial home resort resale to try out at a great price, and have since expanded. (see signature)
My answers in red in here:
1. I would plan to go at least every 2 years and buying 50%ish of the points needed. I'm really nervous about losing a whole year's worth of banked points if something had to cancel.
2. ALL of what @Cfabar1 said!! We bought a lot of VGF points because we love the resort at Christmas (and other times) - others have listed the resorts that are extra-popular over Christmas. My personal favorites because of decorations etc. are : VGF, AKV, CCV. When we go over the winter holidays, we plan dinners at many different resorts to see their decorations and there are often things like carolers and Santa and the like. VGF has the biggest and most elaborate gingerbread house. We haven't been there over Xmas in a few years and I'm suffering from withdrawal.... They also have a chocolate egg display around Easter. In short, the lobby always smells and often sounds amazing.
4. I'd add that there are resale sites have have points calculators that will give you a sense of the # of points it costs for a stay at different times of year, and they are easier to use than the point charts that DVC publishes. Christmas points for large units makes my eyes bleed.
VGF is super hard even at 11 months for Christmas and December (it's fine at 11 months other times of the year) - at almost all room sizes. There are a lot of resort studios now so they're a little easier to get and for a family reunion you'd then get multiple studios... I don't know so much about booking the other resorts at Christmas because if we are going we book at 11 months on the dot at our home resorts. (Have stayed and booked each of our home resorts then, and it's challenging but doable.) 2021 was the hardest because of the pent up demand.
^^ All of this...
Our story: we bought our first contract in 2017 with a 5 yr old and a 1 yr old, and BLT was the only resort that was walking distance to MK. It was absolutely the right choice for us! Now that our kids are older, they are out of strollers and that makes the traveling to parks a little easier. When the baby was in a crib, it was easy to do studios and there's usually a slightly away place for a crib. Then the kids got bigger and it was more luxurious to get a 1br with a kitchen, get a grocery delivery of fruit and breakfast items, and not sit in the dark for hours after the kids went to bed.
Now that the kids are bigger and they've experienced the Murphy beds in the living rooms at Riviera and VGF, I feel a little bad sticking them on a pull out in a 1br (BWV and BCV before refurbs and maybe still?, and also why we still haven't stayed at BRV/CCV). We like the savanna rooms at AKV and have stayed in both buildings - but when we had little ones in the stroller, we avoided using buses as park transportation, so we haven't re-visited AKV until recently.
I really like our mix as our family has grown and our preferences for different sizes and styles has changed - BLT (resale mostly) in a 1br (studios are too small) was great for getting to and from MK with a stroller, and even if we were in our room because the kids had to go to bed early, we could see fireworks. Our next purchase was VGF (resale + direct) - despite wanting BCV/BWV to get something walkable to EP/HS, I was scared away from the 2042 end dates. Then RIV (direct) because we did want EP/HS availability.
With one young child and possibly another one in the future, you'll have stroller considerations for a bit - it's kind of a hassle to fold a stroller and carry it on a bus, so then MK-area resorts might be more appealing. Also, while AKV does tend to have availability at 7 mo, if you're buying to use in December and especially Christmas, you should plan to buy a home resort that you like for the holidays. For me, with little kids, I wouldn't want to have to bus any time I wanted to go anywhere. CCV/BRV have less-than-ideal bedding situations in larger units (some sofabeds, 1br only sleep 4, etc) that you should be aware of, all BWV 2br are lock offs so it can be hard to get them, BCV's feature pool, Stormalong Bay, is hard with littler kids but becomes a lot of fun once the kids are older and strong swimmers. We have yet to stay at OKW/SSR because my kids want to be in the parks ALL the time.
TL; DR: if you're really planning to use for family over Christmas at WDW, a WDW resale contract at about half the # of points for a typical stay might be good for you to start with.
For
Disneyland: You can book VGC if you see a random night pop up, or you can rent points, but there's off-campus options at DL that are pretty convenient too. We've had very good luck booking (and more than once) AUL, VGC, BCV and BWV and AKV at 7 months, and we liked them all. I love DL and VGC but - I've held off buying VDH because of the transient tax, and so far have managed to book VGC* with my much cheaper WDW points, so I've deferred that issue for at least another 1-2 years.... (*going to be there over Christmas in a 2 br that I booked at 8am, 7mo, on the dot)