Jeff,
I run .340 necks in my chambers. My next ones may be different if I do chamber up another barrel but that's yet to be seen.
While I do have a big neck, I run a .328/.329 loaded round size, so I take a lot of brass off.
Now again, I run all Norma brass but there's plenty for me to clean up there, or even if I was to have a 334 loaded round I'm sure. From past experience, I'd say the necks on the Win brass are actually thicker and will need more brass removed, but all the WSM brass has changed over the years and that might not be true any more. Probably buying a bag of brass or asking someone here who shoots newer Winchester 300Wsm brass would give a definite answer to that.
If memory serves me, .020 of neck material on new brass was not uncommon. It was in fact so bad, reloads would not go in a sammi spec factory chamber sometimes without neck turning. By now I hope that's been fixed with the Win brass.
Oh, and I'd be the wrong guy to ask on that freebore length as my boattail/bearing junction is WAY below the neck/shoulder junction when a bullet is seated.