Your .357 will do the trick.   If you handload you have tons of bullets to select from.  Honestly, I wouldn't bother with anything bigger than a .44
Granted our PA blackbear are some of the largest taken in the lower 48 each year, but your typical 200 pounder will fall just as quick hit with a .357 slug as one from a .500. Besides you'll be able to handle it much better.  Accuracy is the key when hunting those critters, not just pluggin holes in them with a BIG round.
If you do run into one of our 600 pounders, then you'll probably wish you were toting a rifle instead of a handgun anyway. 
 
I wouldn't waste the money on all the hype.  If you just have to buy a new handgun, I wouldn't go the route od the 500.  I actually prefer hunting deer with the .357 over the Ruger Redhawk .44 only because the .44 is almost too big to carry with a shoulder holster.  Sometimes I feel I might as well be carrying a rifle as that heavy thing.  And it's way smaller than the .500 S&W.
It does the trick though
