First, Shawn doesn't really know what he wants, and I think VdB/RdB is probably not appropriate. He's trying to maximize his space, and common figs like those would be easily accessible.
What I suggest is that Shawn come to the next Wolfskill tasting and get an idea of the range of flavors--which isn't that wide! It amounts to honey and melons, supersweet or not/berry, supersweet or not/molasses, supersweet or not/sort of sugary-peachy. Intense flavor or mild? Then how juicy, and how crunchy.
Next pretty much comes vigorous tree? Productive tree? Ripens well in a marine climate not as hot as interior California?
I would suggest that Shawn be okay with one crop figs as well. Essentially VdB and its cousins are the only commonly available varieties with both an excellent breba and main crop.
I suggest, in absence of your tastes, Shawn, that you get two figs. The usual Black Madeira, which I'm pretty sure does SD well, since it was in the retail trade of SD nurseries for a long while. The other should be, Gulbun, 278-128, Atreano, a nice supersweet honey type that's relatively early... Idea is intense, super sweet berry tree with amild berry or honey, maybe supersweet, plus earlier than Black Madeira tree.