I share your take on this. When we bought Direct in 2010 we had no idea that there was a resale market.
I stumbled on to the disboards while chatting with someone on a cruise chat site. I am so glad that I did, but I have no regrets in making that initial Direct purchase. Having those benefits have saved us quite a bit since 2020, with APs, MM events, even gave me the opportunity to book early for SWGS when it opened last year. I have added on several times, both resale & direct, and I agree that buying the best resale contract first makes it easier to match use year direct. However, our first DVC guide (Rafael Massa) was thorough and knowledgeable, and suggested our use year based on our preferred travel dates, and that has been a blessing. I would not have thought to do that on my own. We use DVC a little differently than a lot of folks, in that its primarily for snow-birding as retirees. We head south for winter every year, and its been working out very well. This year we spent 50 consecutive nights in studios at AKV & SSR. We have 49 Nights booked for 2024, and are waiting to close on our newest resale so that we can tack on another 2 weeks annually, and stay at WDW until mid-march. Best retirement option for us. We show up via DVC, hop from resort to resort, and head home when we're done. No utility bills, no property taxes, no insurance, no property management fees, and no worries about possible storm damage. Prior to our retirement, however, we used DVC for 10-12 Nights vacation each year, and we still believe we saved money over vacationing the old-fashioned way.