That's a good list CB, #2 (road) is a good point. Personally I would say that the bear spray is unnecessary however he might run into a stray/unleashed dog. A talk about how to handle aggressive dogs would be useful if he is not familiar with actions to take. Alligator
Good Point. Unfortunately I have had a few close calls with agressive dogs on the trail (although the vast majority, along with their owners, have been well behaved) and we have talked about it. He has also been witness to the loss of some of our livestock at the hands of semi feral dogs, so he knows what they can do. If hiking poles don't stop agressive dogs, then the bear spray might indeed come in handy.