TBH, I don't think it matters what your skin colouring is, I think anyone can pull off all colours of UGGs.
I have the short chestnuts and I love them. <3 I don't see the point in paying extra for a little bit more length. I also love the chocolates and blacks, so I can understand why you're having a hard time choosing lol. I'd say chestnut would go with more than chocolate though.
I the Sundance UGGs, I would've bought them had they not been so expensive here.
My first pair was the Chocolates. But right when we started walking out the door the sales lady was like, "Wait! I just found these others, reduced price!!!" Then me and my mom just turned around and looked at them. They were reduced to $50 because it was the display model & one was faded, but then she put the other under a light for a couple months & it then matched the other! So we really couldn't tell! So we took them, I love them, but its a bugger to keep clean. I manage though.
I am also asian with dark hair. I have both the chestnut and chocolate. They both go with everything. I love the color of the chestnut but I like the chocolate ones because you don't have to worry too much about getting them dirty.
As for the Sundance II. I have those and they are very comfy! They are a bit heavier than the regular classic ones though, due to that harder sole. They really are cute and you don't see them as often. I also think they are actually made for snowy weather, unlike the classic boots which aren't made for wearing in the snow at all. The classics are just a cold weather boot.