Large caliber question

As of today I have never killed an animal. My mom is engaged to a hunter who has been to Africa a half dozen times and has many grand slams of all different species mounted on his wall and I have the bug to hunt bad. I currently have 2 deer tags for this year and am anxious to get at it. One of the reasons I was thinking of the 338 caliber choices is because it's considerably different than the 30-06 whereas in my opinion (looking through various ammo charts/ballistics programs etc) something like the 300 win mag is too similar to what I have to justify the cost of buying it. I have an AR-15 for the smaller animals/plinking/etc.., my 30-06 that I will be loading with 208 Amax, and I'm looking for one step bigger to complete my collection (for atelast this year :)). I will primarily be doing target shooting out around 800 yards but also like the rifle to be able to be carried through the hills on a hunt (so something like the 110 BA isn't an option at this point).
 
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