While one key question is what type of bear, but the other equally important question is just how much shooting have you done with any of the calibers being suggested. I think it is very unwise to suggest anyone who had no experience with heavy rifles should start out with a .338 of any kind, let alone a .375 H&H.
What shooting have you done, jc? What experience do you have with various calibers and rifle types? Find out what bears actually live in the country you will hunt.
If black bears are the animal in question, anything bigger than .30-06 is completely unnecessary.
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