Here is my conundrum. I have an '08 Surly Cross Check that I picked up off CL about a year ago. The previous owner built it from the frame, but more as roadie group ride bike. He had 23 tires, Dura Ace 52/39 cranks and 12-25 cassette. He had less than 500 miles on it and instead bought a lighter Specialized.

Anyhow, I need lower gearing. A lot lower. I was thinking either the new Velo Orange Grand Cru (46/30) or the Sugino XD2, both with something like an 11-32. Doing this would likely mean new crank, new FD, new RD, new cassette, and new chain. That could add up quick.

Then I noticed the Rocky Mountain Sherpa's are on sale. I saw the Sherpa 10 for $959. It already has a triple (though I'd probably have them swap for a lower one) and a 11-32. Plus, eyelets on the front fork.

I was thinking it might be easier/cheaper to buy new and sell the CC on CL rather than upgrading the entire drive train. What do you guys thinking? And could I even sell a CrossCheck? I don't Surly's often on CL.