RE: 338Win Mag or 375H&H Mag
I shoot the 338 now, after graduating from a 308. Yeah, the recoil will get you at first, but you learn how to master it and then its just great.
Looking at bear thugh, and generally shooting under 200 yeds, I would go with a 375. Around 200 yds the 338 starts to crowd the 375 and becomes a more general over all weapon, with slightly better trajectory and it also has better foot pounds at the long range.