I don't know Canadian law, but I think some of the women he messaged could collectively make a case of harassment/ sexual harassment, as clearly that is what it was.
Further to this, some of his comments relating to children - while not criminal in of themselves - indicate at least the desire to engage in illegal activity with children. I think he would have a hard time convincing a jury that teaching a 12 year old girl, who is a stranger to him, how to use a tampon in public toilets isn't due to some weird sexual fantasy. Plus, didn't he run a competition where he encouraged young girls to go topless or something insane?
I'm pretty sure he's an actual predator on some level, either that or this is the most retarded and self-destructive attempt at trolling ever - in which case he needs to be put in a fucking asylum before he can hurt himself any further.