I concur. Why is the state of human interface design so utterly deplorable? With great hesitation, I downloaded the version 2 of Skitch. Mistake. "Spiffy" interface = hard to use. Impossible to not have shadow on font (and, no surprise, no font choice at all). Really basic stuff. And yes, I do know that it's "not Paintbrush". But it's barely a drawing program. Sigh. Back to the drawing board. And replacing V2 with v1.
Regarding support: I think it's worth keeping in mind that what we have here is a largely free product from a small organization. I have no idea how many premium users there are, but I doubt it is enough in and of itself to foster a huge backend customer support structure. I've not had good results either, but I just accept it and move on.