RE: Which Handgun
The .40 S&W is my handgun caliber of choice, particularly for carry. My favorites are the HK P2000 and Steyr M40A1, but there are plenty of other makes and models out there in that chambering. For carry while hunting, I would recommend sticking withgood 180 gr. JHPs.
As for bear, I'm sure a few well placed hits with a .40 S&W would do the job, but I'd feel better having some extra power with a .44 Mag. Ruger sells some really good revolvers at excellent MSRPs. You can also use .44 Specials at the range so you don't wear yourself out with the heavy magnum loads.