Hahaha, this is a good question! I’ve never given him much thought before. 😛 I’m not sure if there’s much logic behind him besides being a “mascot” for the mountain vacation destinations (lumberjacks + mountains/forests go together, I suppose?). Even as an American I can’t think of any other meaning to ascribe to him. (But that could also be because I am a city kid who is uneducated in the ways of the wilderness. :D)
But you’re right, he is funny. I especially like this lil tabletop version:

😀