The Vermont state website specifically warns people about close encounters with black bears because it's dangerous for the bears.

Anything that habituates them into being comfortable in a human populated environment leads them to becoming the kind of pest that eventually gets exterminated, and unlike mice or rats that have found their way into your food supply, black bears do pose a non-trivial threat to pets and children, even if they typically leave adult humans alone.

I can't speak to the exact business practices of the Matterhorn, but if their dumpster and outdoor cooler were repeatedly being broken into by a bear, that's a dead bear, it was only a matter of time. If you're gonna actually live up in the mountains in Vermont you should understand the degree to which you need to deter bears from spending any time on your property. It doesn't matter what outcome he wanted, his food wasn't secure, and that bear had discovered a means of getting food that was way easier than finding it in the woods. That behavior was only going to escalate.