We definitely don't have regrets on direct vs. resale. We have 318, all direct. We have 118 points at Copper Creek in a Guaranteed Week that we bought in 2019, and 200 at Riviera (split into a 130-point Guaranteed Week contract and a 70-point contract) that we bought in August 2020.
We started looking at
DVC in probably 2017, but we researched for a while and held off, thinking we should wait until we could pay for it and not finance. Even back then though, given we had two kids in day care, we probably needed to wait even to finance. We ended up buying in spring of 2019 because we had decided we wanted to own at Copper Creek. Our intention was to only buy the minimum for direct benefits (at the time it was 75) then add on a resale contract a little later. We ended up digging into Guaranteed Week ("GW"), and we went that route instead. (Our week is the week after Thanksgiving, usually.) The funny thing is, we have yet to actually use the GW, although we may this year if we can't get into Grand Floridian that week - at this point it looks like we'll have to waitlist since it's already not fully available and we're 9 months out.
We stayed at Riviera in early 2020 and really liked it, so we intended to add on at some point. We bought sooner than we thought we would have in August 2020 because the discounts were really good (we paid $160/point).
For us, we've actually been able to take advantage of the direct benefits and bought Gold APs in 2019 and have kept the renewed, so we still have them (obviously the name's now changed). Losing APs is honestly one of our bigger fears because the access to the cheaper pass makes it worth it but also allows us to go more often than we might otherwise - or we'd have to go for the regular pass which would cost us significantly more. So for us, that's saved us I believe over $1,600 per year for a family of 4.
Honestly, I'd almost feel a bit of regret over waiting a couple years to pull the trigger, thinking we needed to wait to pay cash, since the price per point went up $20 during that time, but it worked out pretty well because we have the resort we want more (CCV vs. Poly) and a contract we might not have fully researched at the earlier time (the Guaranteed Week), so really no regrets there. I'm also really happy we pulled the trigger on the Riviera add-on when we did, since it's now $43 more per point (with incentives).
That's all the justifying rationale - honestly, I have no regrets because, while we could have saved money and bought elsewhere resale or waited, putting aside whether I agree with Disney's approach to restrictions on resale, I like the peace of mind that we have no restrictions of any kind and I don't need to think about where I can use the points, etc. Owning DVC has allowed us to take even more Disney trips, and we love that. While part of it is simply paying extra for a status or a level of comfort or peace of mind, I'm willing to accept that. While I always thought we'd eventually add more points through resale because of the value, there's a part of me that realizes if we add more, it might be direct again just because that's what we want - yeah we'll pay more, but we already give Disney a ton of money - far more than needed..