I've bought into DVC 3 times. And I wish I had had the funds to buy it all at the start! But alas I did not. My first purchase was in 2009. My last purchase was in 2016. All has been with Animal Kingdom. We travel with a big group usually (10-12 people), so AK is important to me because the points are pretty economical across the portfolio and at the 11 month mark, I can almost always guarantee any room that I want - be it 3-person suite or Studio. My point in saying that - you need to think about your long-term use cases for where you want to buy. Does the resort you want to buy into have the flexibility that you need as your family grows and changes? It can be a pain to travel from AK sometimes to all the parks, but we've always been able to find a room when we pre-plan.
When you go to buy your points, have a discussion about when you are traveling and changing your reservation from your current resort to a points resort with DVC. Because you are still in the purchasing phase - DVC sales reps almost always have access to inventory to do that for you. But you must do it on purchase, not a few weeks later.
I am jealous about CCV. It's the first time I've considered selling my points and buying a new resort. Good luck and let us know what you decide.
Also - I personally made the choice not to go resale. I initially bought into DVC twice before the rules got a lot tighter regarding what you can do with DVC points depending on how they were purchased. For me I didn't want my third set of points to have mixed restrictions - truly personal preference because I have used them to cruise. But with current resale pricing versus current costs per points, it makes a lot of sense to do a cost break-even analysis.