Updates... I finally got the rider swapped for a drop bar. I used an 80mm 7 degree stem and went with Sora shifters as all of the 3x9 Ultegras on ebay have been beat to hell. I'm not a huge fan of brifters, but they were surprisingly easy to install and tweak... and there's not too many other options besides barcons on this setup.
So far, this is the best thing I could have ever done and makes me not mind almost everything else about the bike that I was considering changing. Surprisingly, the Sora levers have better braking with the stock calipers than the ones that shipped with it. That was a pleasant surprise.
The paint's getting all scratched up. As a commuter that gets thrown into the back of a car 4 days a week, locked up in a crowded bike area and carried on a train, that's to be expected.
Sorry for the photos not being great... took them after a quick ride this afternoon.