It's late for me but one difference I can think off the top of head btwn the two is that the base Crosstrail will not have a lockout front suspension (Sport version will, though, abt $100 more retail). The Roam 1 will have the lockout. Going from memory here, so double check your specs.

Given your riding conditions, it sounds like if you get something with a front suspension fork you will likely prefer the lockout since you'll be primarily on the road.

Off to sleep now, but maybe bumping your post to the top will elicit more replies.

Oh, and welcome!