I love Titleist's Canadian bag. But I would probably roll with something else if I were to pair it with a clicgear. I've got a SunMountain 3.5 (essentially the same thing, i believe) and while it fits on the cart with no problems, it's much easier to put clubs in and take them out if you can maneuver the bag--hold it upright or whatever. In a fixed position, and with a slightly more limited access to the bottom section (area adjacent to the cart), it could probably get to be a PITA. BUT, as that's not the point of the thread...
I vote black. If the shades of red are off, the whole "look" can get disjointed. Plus, the cart ought to last a lot longer than the bag. It'll be easier to coordinate your next bag if you roll with the black cart.
Enjoy!