I'm highly skeptical that O'Leary would win a general election.  He is too much like Trump, and most Canadians abhor Trump.  There's also the fact that we will have the opportunity to watch Trump screw up left, right & centre well before the next election.  Getting rid of the ACA will rub Canadians the wrong way, and will shaft the working poor in America.  His meddling with Dodd-Frank could well unleash another recession, and his first major initiative -- this travel ban -- has been shot down by lower courts and when it makes it to the Supreme Court, it will likely be shot down there, too.
However, it is possible that Trump policies could do a lot of damage to the Canadian economy, and if that happens, well, few sitting P.M.s have survived bad economies during elections.  
Like many people I was quite surprised by Trump's win, but at least in Canada we will likely see the train go off the tracks and take a step back from naive, arrogant, loud-mouthed populism.