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I'm actually looking around for a fixed gear bike to ride around D.C. (or Chicago, if I can't find a job in Washington) this summer. I'm down with irony.
Sorry, I'm rushing out and don't have time for a complete post, but i think a CYCLOCROSS bike would suit all your needs. Drop bars, almost roadbike, but with a much more forgiving riding position and tires that will be able to take you off the road.
[*]A Cyclo-Cross bike has Canti-Lever brakes, for a wider tyre clearance, but these breaks are less powerful than standard road or MTB V-Brakes, anyway they can stop you, but you need to apply more force on the brake levers.
Nice! This is turning into a bike Appreciation thread. Gets my blood going. It's been a few years since I last rode a real bike (GT Zaskar LE, stiff as a pole).
No one has mentioned frame material yet. I am going to assume, comfort is an issue. Outside of seating stance, I think frame material plays the biggest role. I would stay away from aluminum. From there, your price point will determine, i.e chrome moly vs. titanium, etc.