Good News, Bad News
The bad news: My transmission is most definitely in need of replacement, but my mechanic told me to get medieval on VWoA's butt, because I have complained since the car was still in the break-in period that this was a problem. The slam into 2nd is a known defect.
Seems my comment to the salesperson when I sat in the dealer's lot was accurate. I was lamenting the fact that I loved the color, but the car was automatic and said "It should be illegal for VW's to be automatic." Apparently, VW does a crappy job on them. The manual transmissions are probably the best the mechanic sees, very few problems, but without fail, if it's a VW with an automatic, he will be doing transmission work on it.
The interesting part: the average mileage for this repair is 60k. Mine just turned 130k, so I got more than double (well, about double, honestly) when this became a big problem.
I'm already fired up from other fronts, so the pit bull phone call to VWoA will be quite interesting.