2013 Kona Jake, 2008 Kona Major Jake, 2013 Kona Jake the Snake, 2006 Kona Kula, 2012 Ridley Excalibur, 2008 Surly Long Haul Trucker, 2001 LeMond Buenos Aires
The geometry is fairly different between the Roper and the Cross Check. The Roper has a shorter top tube and taller head tube, so you'll feel less stretched out on it. That's a matter of personal preference, so ideally you'd ride both bikes to see which feels better to you. I'd go with the Roper for this reason alone, especially given your secondary uses for the bike.
The difference between STI shifting and bar ends is also a pretty big factor, but again that's a personal preference more so than a straight up advantage one way or the other.
To follow up, I wound up buying the Surly as my local REI was not authorized to sell Raleigh products in my area.
Thanks for the good advice, if REI had both I would have ridden both then decided, I feel like I got a good deal on the Surly andI dig it even though I'm sill getting used to drops and barcons....
What size did you end up getting? I recently got a CC at the REI sale as well. I've been having a debate over my sizing (ended up with 54 and I'm 5'10"). Also my first bike with drops. I felt like the bars were too low but after a couple of weeks I'm starting to love it more and more. I have really grown to love the bar end shifters and friction mode shifting.