Plainsman,

In answer to your Q' s.
By the numbers, a 338 is nipping right at a 375HH' s heels. At the bench, the 375HH " jumps" significantly more. In the field, the " slap down" factor with a 375HH, to me, is significantly more than the energy numbers between a 338 and a 375 would indicate.

On the other hand, 338WinMag ammo is common and cheap, it is available in a medium length action rifles, kick is moderate, and the rifles are generally lighter which helps in tough terrain and they have plenty of penetration and slap down factor for N.A.

If I had to pick one between 338WinMag and 375HH and give up the other, then I would truly be in a quandry.
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If you are serious about " Kodiak or Afoganuk Island for the big bear" then here is the question. Given that THOSE bears can bite and hunt back, are you going to wait until you actually draw the tag and then in the six months between the draw and the season go about the business of rounding up the $$$, buying the rifle, scoping, practicing with it and THEN go after Mr. Brown Bear with NO KILLS under your belt? OR Would it be wiser to acquire the rifle, get it tuned up, put some kills under your belt on other game like elk or moose and THEN put your life in harms way?

EKM