Couple of thoughts for the author.
First, O'Leary will have his 30% of the vote locked up (as will any Conservative candidate), but so what.  How will O'Leary realistically attract the other 70% to push the Cons past the Liberals?  I just don't see it, especially once a few months of Trump tweets and actual Trump management in power have gone by (remember Trump hasn't had to actually manage or lead anything yet where he is responsible to others).  Running a business vs a govt are miles apart.  
Second, not speaking French is a big issue, it shouldn't be, but it is.  PQ will love that.  More Quebec battles?
Third, not sure how O'Leary - Kenney comparison makes any sense.  Kenney is a real social conservative, not O'Leary.  Kenney is seeking power where there is a traditional conservative base, O'Leary less so.  Kenney has no business skills, but an excellent ground game of young bootstrappers for ground game support.  O'Leary is a business person with no political ground game, yet.