Arrow,
it seems like you've got some questions a bit jumbled here, or else I'm missing something somewhere. You're discussing headspace issues when we talk about bumping shoulders back, but the seating to match the throating is a spearate issue entirely. Yes, seating to a longer OAL would theoretically give you more powder space in the case. Whether this is enough to be noticed in the field, I have my doubts about that. Standard OAL for the 308 Win is 2.850" as a max, and yes, you should be able to load out to 2.990" and still have some grip on the bearing surface. You may or may not have tension problems, depending on how you're using this ammo. Howver, I seriously doubt that the added capacity you create by doing this is going to be worthwhile compared to the potential problems.