RE: Do I need a .338?
Having hunted deerpretty extensively on Kodiak Island in the early 1990's, I'd have to say the .338 is an excellent choice. I used a 7mm-08 and .375 H&H, depending on the bear population of the area I was hunting.
That being said,there's a new kid on the block that I would pick above any of them: the 325 WSM. It's a short action that comes in a LIGHT package. Alaska hunting is a lot of up anddown, so you'll really appreciate this. The 325 is enough gun for a brownie also. A brand, spanking new Model 70Featherweight or Browning A-bolt can be had for under $700.