Shawn at the Bicycle Center is a magician! I showed him the unhappy stem and we talked numbers, and came up with a replacement from Origin 8!
The new stem is perfect! Not too long and not too short. The perfect angle, too. While on my test ride today it was great. I was a bit premature in re-wrapping the bars because the left brake lever is a bit too high. On top of that I think I need different bars. Either bull horns or regular drop bars.
I ended up going back to the original set of bars that came with the bike and the following day I decided to ride the Paramount to work. Everything felt great. The hoods were now in the right place to get the leverage that I needed to climb and it just feels much better.
In order to minimize the climbing because my gearing isn't conducive to New England, I extended my route home to avoid climbing back up Newtown Turnpike and in doing so ended up with a round trip total of 62 miles, or a Canadian Century.