One other point, if a bullet of a given weight is made in a smaller caliber, it will have to be longer. A longer bullet will need a tighter twist to stabilize it. The twist of the Contender barrel may not be tight enough at the velocities obtainable to stabilize the bullets.
New ideas are great but I doubt this is a very new idea. I certainly don't care if you do it, by the way. My dream is to have an Encore handgun made up in 375 Weatherby Magnum or maybe 416 Remington Magnum; not what a lot of people would call smart or practical. So, really, go for it if you want to and have fun. I'm only trying to point out what I perceive to be flaws in your plan.
As far as bearing surface goes, if you take say bullets weighing about 160 grains in calibers .308 and .284, the .284 caliber bullet will have a longer bearing surface, a higher ballistic coefficient and will require more pressure to move it down the bore. The point I was making is that your quest for better performance via a higher ballistic coefficient would probably be frustrated because you wouldn't be able to obtain as high a velocity at acceptable pressures. The only thing ballistic coefficient gets you is better retained velocity which is good but if you have to start out slower to begin with, you've gained nothing.