Just curious, what made you decide on a steel frame? All the talk about the smoother ride? Make no mistake, they're ALL stiff. May as well get one that is corrosion resistant without any extra treatment on the inside.
I was leaning towards a Cross Check too. But the Specialized TriCross Sport has an aluminum frame, carbon fork with Zerk spacer, equal quality derailleurs, and brifters instead of bar end shifters. The stock seat was replaced with a Brooks Champion Flyer, which more than makes up for the difference between steel & aluminum frames when it comes to shocks going into my bum. I suspect the stock saddle on a Cross Check would also need replacing pretty quick with a Brooks.
If you're really stuck on the steel frame, another one to consider is the Gary Fisher Lane. It has the brifters too.
I bought the TriCross as a second "upgraded" bike, but my commuter (the SC3) is still much more comfortable, and pretty fast too. Maybe that will change when the Brooks is broken in.