Looking to buy a medium caliber rifle and large caliber rifle, Any Suggestions?

As long as you are going to get a bigger rifle as well as a medium one I would go a little smaller with the medium one. What I would have in mind is a Savage 16FCSS in 260 Remington. It is stainless and synthetic and Savage is building some of the best rifles you can find these days short of going custom. As for the larger rifle, the Kimber you suggest would be great although if you are thinking about going after the BIG bears someday then I would go on up to the .338 Win Mag.