If O'Leary wins I strongly doubt he'll win a general election.  It is simply a reality in Canada that if you don't win enough seats in Quebec, you're done, and you need to speak French to win enough. 
Regardless of Trudeau's efficacy as P.M., even his detractors have to admit that he caught the moderate, tolerant and generous nature of Canadians very well and rode it to power.  I don't think O'Leary can do that.  We have never had patience with bombastic types and don't have the "default anger" Trump, Le Pen and Brexit tapped into so well.  When some of the Cons -- Leitch in particular -- tried to play the loud 'hard right' card, it blew up in their faces.
We also know very little about O'Leary's policy ideas.  Where is he on the environment, social programs, health care, military procurement, multiculturalism, federal-provincial relations, relations with First nations, the Middle East, etc.  These are things that will matter more than how many times he can call Trudeau "surfer boy".