Nothing wrong with packing an N-frame 44. The extra weight over a K/L-frame 357 (and significant power differential in the case of 44 mag) just seems unnecessary in most cases, so why lug it around unless it makes you feel safer. If you're just hiking and have a good gun belt and holster, no big deal I suppose. But if you're backpacking you're probably already carrying more than enough weight. Speaking of which, that's a very nice Ruger

Life is full of calculated risks that we all have to assess for ourselves in the end. In the above story, it sounds like you got away without firing a shot and then reassessed your choice of woods gun because the black bear was unimpressed with your model 65. Would the 629 have made a difference? That's not just a rhetorical question. I've seen their tracks, but not having ever encountered one in the wild, I'm seriously curious as to whether one or two hits with a 357 magnum fired in less-than-ideal circumstances in a hurry (meaning possibly no CNS hit) would stop a black bear that for whatever reason has become aggressive.

For the OP: I'm going to go out on a limb here and say if you live somewhere where black bears are the largest wild animals and you think an encounter is likely, bring bear spray in addition to the firearm of your choice. If you're backpacking, think ahead of time about how and where to store garbage and food at the campsite. A park ranger will tell you that black bears aren't aggressive and if you have to shoot one, it's probably your own fault. Fortunately, I wouldn't know.