We purchased 250 points (semi-loaded) resale about 14 months ago. We are very happy with our purchase, and we saved about 60% or more over buying direct...
We are just about to take our 3rd trip using our points. Last January we treated my wife's parents (OKW 2BR). This December/ January we are treating my parents (OKW 2BR) and my wife's brother and family (he and his wife have triplets-- we're staying at the treehouses and a SSR studio). We also did a quick SWW trip last year. We purchased one annual pass for the three trips, and we've borrowed points to do everything and to invite everyone. If we paid 30% rack rates, we've already come close to breaking even. Our points will be almost completely depleted for 2012 by the end of this trip, but we've had 3 vacations and invited three other families to join us as our guests. We could not have afforded this without a discounted resale contract. If we had purchased directly from Disney, it would have twice as long to break even.
We don't care about using points on cruises or exchanges, so the limitations are not a big deal to us (even though we're grandfathered in at present). We're probably buy another contract in the next year, and we definitely plan on buying resale.