Before we bought in, we debated on this as well. Our thoughts were that the annual pass discount is a
predicted savings in the most ideal circumstances, but the savings you get buying resale is an
actual savings now. We predicted on spreading out our annual pass through 2 visits and buying every 3 years. But if something comes in the way and we have to skip a year or two (like this pandemic) or if my kid decides not to join us in the future, it'll just throw that number way off. We also predicted the savings off the life of our contract, which for PVB is until 2066. Although everyone would love to hold onto their contracts until the end, realistically, I'm not 100% sure I will.
At the end we bought resale for the actual savings and then the minimum direct (75 points at that time) to appease our FOMO.

Good luck on your decision!!