Hey Natheless
I have the Surly Cross-check. First if you want a good strong steel bike they rock. They are heavy though so if you are looking for speed you may want to try a lighter road bike. I bought mine cheap and have rebuilt just about everything on it. I recently put an XT rear derailleur on and a new touring cassette. I can put fenders on, a rack and you can run fat tires on it. I think if you can find a cross-check and a long haul trucker I would try both since they fit differently. You can also check out girlbike.com and Crystal has a picture of hers set up. She started with a cross-check also and went to the Long Haul Trucker.
Hope this helps.