We own Riviera and have done studios, 1B and 2B. All are really excellent. We also love CC, but we often travel with family, so usually a group of 5. I guess I'd play out where you think your family's future needs are?
We bought in expecting to do studios, got upgraded during Covid to a 1B and never looked back. We thought we'd be happy in 1Bs forever, then started bringing extended family in a 2B, our boy/girl kids are teenagers now and tall/want privacy, and I can see us even traveling as a family of four in a 2B sooner than later so they can sleep late and I can putter in the common kitchen area in peace and quiet.
I think you'll be only happy in a 2B anyway, as a family of five, but I know some folks are studio stans forever and hate the idea of blowing points on anything bigger.
Would you ever want to go prime weeks in early December? My understanding is every room category except the cabins go super fast, so you definitely would need to own there to stand a chance.
Do you think as the kids age out/get busy you and your partner would want to do a couple's trip in a studio? An argument can be made for both resorts that they're hard to nab; Riviera for the resort view and CC because there's so few of them.
I think
@Brian Noble brings up a good point; CC 2B is comparable to a Riviera 1B points-wise, so where would you be happiest?
I agree with
@Sandisw that the resale spread is not that big of a deal, at least to me, and I do think Riviera is going to get a bump up once it's sold out and LSL is added to the mix of restricted resorts at WDW. The CFW don't really matter in my mind because they're so new and niche, but LSL will be a huge resort restricted, and VDH being restricted, this seems to be the path forward that they're not backing down on, so I don't see the resale as being a huge impediment. We have already broken even and then some on trips on our Riviera points, so everything now is gravy as far as I'm concerned.
Buy where you want to stay. I think Riviera has the better dining options, but WL is not bad by any stretch. The pools are cooler at CC/BR, but we love Epcot and HS and the Skyliner. Both resorts are peaceful after a long day in the park, which we LOVE. Do you mind bus/boat as transportation options? Do you think you'd use the walking path to Fort Wilderness if it reopens? Both resorts are really great, just different. I do feel like Riviera feels REALLY spacious. CC 2B seems tight to me for a family of four, so five seems a little meh to me, but that's just my impression. I haven't had a chance to try it because we can never grab it!