It's funny you mention that, because Bicycle Space is literally next door to my new office, and I have their group rides info stuck to my fridge at the moment.

That's exactly what I was thinking about, re: getting used to riding on the road. My wife and I are going to check out DC Vintage Cycles this weekend to see what they have to offer. At this point, instead of trying to transform the mtb into a commuter, I'm going to keep an eye out for a commuter-ready bike, with fenders, chain guard, etc. I'm hoping those guys will have something useful for a nice price.
My wife's going to buy a used bike as well, just to ride around with me every now and then, so I'm excited about the group ride concept.