I am currently facing this choice myself. I think a great deal depends on how you want to use the points.
We go to
Disneyland quite frequently for short little weekend getaways. We currently own at SSR -- bought direct years ago, but now we need more points.
Currently, when we try to book on fairly short notice (month or two out), I can't always get a villa at the Grand Californian, but they will almost always be able to offer me something at the Disneyland Hotel or Paradise Pier. So we are virtually never just Sorry_Outta_Luck, even when we haven't planned ahead.
So when we decided to add on, that was a pretty big factor. I use that opportunity to trade into the Disney Collection pretty regularly. So makes sense to buy direct; but I almost never book farther out than the 7 month window. So I am just going to buy some SSR points direct. They are going for about $99 direct (about what I see Grand Californian going for on resale).
So. I definitely thought that I wanted to buy resale. And I really thought that I wanted to buy at the Grand Californian. But I've come full circle! More SSR points for us. The original set has served us well. We have used the points for everything -- cruising, Grand Californian, Animal Kingdom Lodge, etc etc. It has been great.
Would I be happier if I were paying only $80 or $70 per point? Of course. But I think I would regret it next time I didn't have a place to stay in Disneyland. Also: we will almost certainly cruise again. And while I know that's not a super efficient use of points, it works great for us in years when we don't feel like visiting the parks. Especially now that there is a ship on the west coast. So it all really depends on your personal needs.
Which you already knew. So I'm really no help at all.
