Ultimately, only you can decide what is the right decision for you.
I am the type of person who always has regrets, no matter what decision I make, because I over analyze everything, and so I'm always weighing the pros and cons. I love Disney, we spend a lot of money over the years in Disney, the numbers tell me it makes sense for us to be
DVC members, and yet as happy as I am to be part of DVC, I still have moments where I regret the purchase, because I keep thinking I could have kept that money invested for retirement, lol. So I totally get the worry that you will have regrets either way.
I have both direct and resale points. I have Direct for the discounts on APs (which save us about $1600/year), the ability to book RIV and future resorts, and honestly for that "bad option" of using for cruises, ABD and other options should the rental market bottom out. (Right now, if I decide to do other trips, my intent is to rent out points to cover those other trips, but I wanted the option should renting not be viable in the future). I also picked up 2 Fixed Weeks to secure those critical Thanksgiving and first week into December weeks at Copper Creek. I have resale for the significant upfront savings on adding on more points, and because I can still use them on the existing 14 resorts.
I was originally against Riviera, and admittedly am the one who is doing the "was this the right choice?" But my husband really loved Riviera based on the sale presentation and all the videos watched of the walk-throughs. We love the Boardwalk area, World Showcase of Epcot, and love the idea of Skyliner access to Epcot and Hollywood Studios. The rooms at Riviera are huge, and even studios sleep 5, which is critical for our family (our two sons won't share a bed). I was turned off by the points cost and the dues. My DH eventually convinced me that the difference in dues is likely not to remain so large, because new DVC resorts don't increase much in the first 3 years usually, and the other resorts will continue to do so. ANd if you look at VGF and BLT, the
point chart is actually less than them. We like the location and the access, even if the theming is different than our usual (we are more BRV/CCV and AKL kind of folks). But because of the incentives, we got a really low buy-in cost for Riviera and that is ultimately what allowed my DH to convinced me to go with the direct purchase -- we'd likely never see such inexpensive direct prices again, and these points can be used anywhere. Admittedly, we have no idea what the resale market is going to look like, but it's not our *intention* to sell these, so we decided to risk it. We did it as two small contracts so hopefully they'll retain better value if we do need to sell.
I recognize this may not help you, but maybe sharing my own thought process might help? At the very least, do listen to your gut, but also consider what are the most important things to you. If you are determined that you are going to own DVC no matter what, weigh not just the financial aspect, but what will make you happy. In the end, it's the happiness - or lack thereof - that you'll remember most down the line (presuming DVC is not a financial burden to you).