Why not just shoot a .338 WM then. I would be curious how the .30-06 shooting a 200 grain NP @25-2600fps so out performs the .338 Fed shooting say a 215 Swift Scirocco @ 25-2600fps, which both will do.
How many bear have you shot with the .338 Fed compared with the .30-06 with bullets of similar construction? I have never hunted bear, I have no problem admiting, but I think I would lean to the .375 Ruger/ H&H if I was hunting something that thought that I was food! FYI in the Finnland and Sweden the 6.5 X55 kills more moose than any other round, so it does not take a cannon to kill a moose.
Well, that's an easy one. With bullets of equal const, the higher Sectionl Density (SD) wins. The 338 Scirocco is a 210 actually, anyway the SD is .263 & a 200 gr. 30 cal is .301, the difference between .263 & .301 is dramatic! Also, the Scirocco is designed to expand wide, which limits penetration even further, so no contest on this one.
Also if you want a fairly flat shooter, a 338 Scirocco with a BC of 507 isn't bad, but the BC of the 200 Accubond at .588 spanks it major!
DM is right, to do better with a 338 bore, you need more powder.
But for Harry's application it's fine.