I have a little more information now.
Apparently the issue must be codec related. After you hit "convert" it will begin decoding the .DSS file, and it will immediately error out during the converting process. I tried it with various codecs on my machine with mixed results. Some of them just couldn't seem to handle it any more for whatever reason. The reason this strikes me as odd is because initially I had no problem decoding using these codecs. Now, all of a sudden, they don't work any more.
I'm certain I could find another codec that works and live with it, but my concern is for the other people that I'm testing it for - I'm wondering why some of the codecs are 'breaking' after a few uses.