RE: 338Win Mag or 375H&H Mag
Hunter40,
Both the 338Mag and the 375HH are an appropriate step up from your 300Win if you're looking for more "slap down" power for big game that can bite back or animals larger than plain jane deer. I have both the 338Mag (2) and a 375HH and love them all three, but favor the 375HH.
The 338Mag runs a real close second to the 375HH in the paper ballistics/velocity/energy arguments and is a real "easy going" gun to shoot. On the other hand, you learn quick that you've stepped up a notch from the 338Mag when you sight in a 375HH. Seems that for the 375HH with only 50gr more bullet weight (300 up from 250), that it is definitely more of a handful in terms of recoil and barrel jump - not nasty, just more - easily mastered with some forethought.
I was thoroughly impressed with the 375HH in last years elk hunt - two shots and two elk down at one opportunity and these weren't the perfect "snipe their heart out shots" that it seems almost everyone on this forum but me makes, both elk laid within 30 yards of each other. (Had two licenses). There is something "intangible" about the 375HH, it may not show so much on paper, but it really performs when its "showtime." I've really come to appreciate why the old (1912) 375HH has remained so popular over all this time.
If the bears come running when you shoot, then I'd definitely go with the 375HH and make sure you stay at the top of the food chain. Here's to welcoming you, in advance, to the "big bore" club!
EKM
Good judgment comes from bad experience! Half of elk hunting is knowing what NOT to do!