RE: first black bear hunt
Depends what type of hunting you intend to do. For short range shots, under 100yards (such as hunting over bait or hound hunts), I would chose the 30-30. Anything else such as spot and stalk I would use the 270. The biggest thing is to be very familar with each gun and know your limitations, which I assume you do because you stated that you've shot each gun lots, so that shouldn't be an issue.