The Trudeau government has done sensible and polite legwork with the Trump phenomenon.  Sending Mulroney, Sajjan and even Freeland to meet before the PM visits.  As long as Trudeau is friendly, complementary and doesn't in any way upstage Trump, it should be fine.  

Japan's Abe did the same and that seems to have worked out well for Japan.  May from the UK tried to get too close and is being burned for it at home, but she's a right wing anti-globalist too so she  competed with Trump for some of the same political air.  Not something Trudeau will face.