Of the calibers mentioned, here's one more vote for the .309 JDJ. I have been running a 165 @ 2400 fps from mine for a dozen years.
Now, theres black bears, and there's BIG coastal black bears ! For the latter I want the .338 JDJ No. 2, or the .375 JDJ if I'm limited to T/C's, although my preference since 1999 has been the FA .475 Linebaugh. Feels better in the Devil's Club and bear tunnels of S.E. Alaska.