RE: Newb Question
 

Sounds like you are interested in shooting from a very familiar place. I would borrow a range finder or otherwise measure off distances so that there would be no need to estimate range for an extra long shot. Another thing to remember is that if you hunt at dusk, it makes it pretty difficult to track down a wounded animal. Your deer is apt to make it to the bush and lie down, but it still will be hard to find in the dark. Going after a bear is another story. Have you observed the same behavior at dawn? Much better time to take a long shot.

RE: Newb Question
 

I think you made a good choice in rifle & caliber. I would recommed that you get a range finder. You will have no trouble killing deer & bear with that rifle.