I would base the decision - if I was making it- on whether I wanted to handload. (I do, so the 375 is great. Otherwise, I'd go 338.) I would also consider the rifle itself - and think the Alaskan is more nicely thought out and put together than the standard, although not by a lot, so the 375 would be my choice there. Cartridge-wise it's about a wash. The 375 gives you a bit more, but the future and availability of the 338 is assured. My own choice would probably lean toward the Alaskan overall. However, I know I would also borrow JS' line about "go big" and opt for the 416 version.
