I haven't lived in big game country in quite some time. The largest caliber rifle I have right now is a 257 Roberts which is ideal for what I hunt. I doubt I'll ever have the opportunity to hunt brown bear, but I have been knocking off bucket list items for a while now. One of those bucket list items is elk or moose, and I doubt I'll be fortunate enough to do that trip in AK, so a brown bear worthy caliber isn't something I can justify even in the unique way us gun owners justify stuff. After my replacement surgery, I'll see what I can shoot comfortably. Right now I am thinking about the 338 Federal. I do my own loading and have an affinity for oddball calibers. Heck, I reckon if I lived in Kodiak again, I'd probably favor the 338 Federal even with a good shoulder.
Paul, whatever you shoot, if you haven't considered them, the Past and Cabela's thick shoulder pads make a huge difference to me. My dad, for example, was pretty leery about firing my 700BDL in .300 WM, but he tried it with the pad and a 1-lb bipod (for at least range use) to add recoil-absorbing weight and didn't have a problem with it. I don't use one, but a Lead Sled or something like that might also help. And given your shoulder's sensitivity, maybe even a removable muzzle brake (using double hearing protection).
Also, if you like the .338 Federal, a semi-auto, like this (http://www.jprifles.com/1.2.5_LRP07H.php) would have further reduced recoil. A lot of people don't like black rifles, but if you don't mind them, it could be a decent option. It might break your wallet more than your shoulder.
