Hmmmm... well let's put it this way. The OP said he had trouble fitting the rack because of the canti brake set-up on his Crosscheck. Which led me to believe that he had in fact the QR Road Rack that attaches at the top via the caliper brake mount and to the QR at the bottoms. If using the rack you have illustrated, then there should have been no problems whatsoever negotiating through the cables with the mounting stays on to the Crosscheck seatstay brazeons. The rack you have illustrated does not fit to the QR.

Either I am terribly confused, or the OP is.