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.