I think this all goes back to someone's previous statement on this thread or another about value. I got a great deal on our first contract, which was SSR, and I've stayed at every resort but OKW, BLT, and RIV on those points, which currently work out to $11.34/pt. And I will be able to do that easily for the next 17 years. After that, all of our kids will be in their 20's, so if swapping isn't as easy DH and I will be just fine staying there.
I also drive an 11 year old minivan. Not b/c we can't afford a new car, but b/c it's been paid off since year 1, we've never had any issues with it, and cars are utilitarian to me, they get me and my family where we need to go. A car is not a luxury item for me, but for a lot of people they are and that's their own choice. DVC is obviously a luxury item, but maybe SSR is an old reliable Honda. I'm good with that, the contract works for us right now in the way we want it to. When/if that changes, we can make a choice as to how we want to proceed.
I feel like I remember at some point you stating or inferring that you are early/mid 30's, married, no kids? If I'm getting you confused with someone else, my apologies. And there's no judgement being passed here. If your life stays that way, then you have an amazing DVC portfolio that you and your partner will enjoy for decades. But should kids come into the picture down the road, it will definitely alter the landscape of your vacations. Sure, they're free for the first few years, but when you start having to buy park and plane tickets and meals the cost of your trips is going to skyrocket. Renting a stroller, Bibbidi Bobbidi Boutique , character dining, balloons, souvenirs, dole whips if you're raising them right...piles of cash. Not to mention the inevitable illness that will force you to delay or cancel a trip, putting points in dreaded holding.
If we had started our DVC adventure prior to kids I'm sure it might have looked more similar to your approach. But it's apparently going to cost us around $900K to raise these little humans, so we have to make some sacrifices when it comes to our luxury purchases.