A 338 for CHRISTmas!!! That wife of yours is a keeper!!!!
I went through much the same thing..including planning a brown bear hunt a few years ago. I bought a 375HH though...my preference...and quite honestly didn't do much thinking about the scope issue. A 338/375HH has about the same range balistically as a 30/06 with a 180gr bullet. Also...dangerous game...like a charging grizzly...uh...hope not..but, I suspect you'll be better off making the first shot count. Also, a good, clear scope with a lower power setting pretty much negates the need for iron sights...though many still use them...I just bring a back-up scope pre-sighted in on the appropriate rings.
So, I went with a standard Leupold VX-II, 2x7x33 and it's just fine...plenty of eye relief, etc. I wouldn't be uncomfortable with a 2.5x8 or a 3x9 or even 3.5x10.....just get one with alot of eye relief!!