The best advice I read on this thread was from Keygrip. Don't plan on getting to the US/Europe on a particular date unless your aircraft is pressurised and deiced, and even then - don't count on it.
By contrast, I've never been "grilled" on the relatively few occasions I've done the flight. The only thing the Canadians seem to care about is that you have sufficient endurance for the prevailing weather, and that you have a current and relevant IR.
Good luck - you'll love it - but take care.