Well, it appears I maybe shouldn't have asked the transmission question. To be honest, all of my cars have been manuals, but I feel like I need to at least drive the DSG to compare. I'm not opposed to either.
The VW dealer in town is trying to sell a carbon copy of my car for $21K, and theirs has 18,000 more miles than mine. I feel like now might be a good time to see what kind of deal I can get.