Smaller contracts do go for a premium and there is no guarantee they'll hold that premium long term...
One thing on the points cushion, my believe is one should buy the extra when buying for most situations, not to go buy additional just to have the cushion. Once one gets to a larger pool of points, I would tend to drop that stance and for some, esp those new to
DVC, feel that often having less than you think you need long term is best. Let's say you're looking at AKV value studios adventure season and you calculate you need 100 points for that, I'd say that 150 pts is likely the minimum reasonable as a new buyer. OTOH, let's say one is looking at the same resort but 2 or 3 BR premier and calculate you need 400 points, not only would I buy less, I'd likely buy a lot less and look at a second home resort. I'd also point out that if one buys a loaded contract, it'll feel much larger for a time and the reverse is true for a stripped contract.