Roughneck,
My dad is a man who has the "Bigger is always better" school of thought, so I can say that the 338-06 is one heck of a cannon for shooting whitetail. I do understand the enjoyment of tinkering on the loading bench however. I'm not sure if you are from that same school of thought, but maybe just think about staying with the 270 as that is a great deer cartridge, or perhaps think about a 6.5 Creedmoor or a .260 Remington. With the high BC of the 6.5 bullets you get plenty of penetration at normal hunting ranges. Hornady has even come out with a high BC 270 bullet (.536) at 145 grains... ELD-X
Just a couple other options for you to tinker with....
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